Hydrochloric Acid → HCID 86654487, compound

HRID 1952432Notes

Reaction equation

HRID 1952432 reaction equation
Cl.NCCCCCC(N1C[C@@H](S)[C@H](NS(C2C=CC(OC3C=CC=CC=3)=CC=2)(=O)=O)C1)=O.Cl.[C:34]([N:41]1[CH2:45][C@@H:44]([S:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C@H:43]([NH:51][S:52]([C:55]2[CH:60]=[CH:59][C:58]([O:61][C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)=[CH:57][CH:56]=2)(=[O:54])=[O:53])[CH2:42]1)(OC(C)(C)C)=[O:35].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.O.[C:86]([O:90][C:91]([NH:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98]C(O)=O)=[O:92])([CH3:89])([CH3:88])[CH3:87].C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C.CCCCCC>[C:86]([O:90][C:91]([NH:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][C:34]([N:41]1[CH2:45][C@@H:44]([S:46][C:47]([CH3:49])([CH3:48])[CH3:50])[C@H:43]([NH:51][S:52]([C:55]2[CH:60]=[CH:59][C:58]([O:61][C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)=[CH:57][CH:56]=2)(=[O:53])=[O:54])[CH2:42]1)=[O:35])=[O:92])([CH3:89])([CH3:88])[CH3:87]

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 86654479HCID 86654479, compoundHCID 86654488HCID 86654488, compound

Product 1

HCID 86654487HCID 86654487, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

YHJ-7-52: (±)-N-(6-Aminohexanoyl)-trans-3-(4-phenoxybenzene-sulfonamido)-4-mercaptopyrrolidine Hydrochloride. To a stirred solution of 1.5 M HCl in ethyl acetate (1 mL) was added (±)-N-Boc-trans-3-(4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (200 mg, 0.39 mmol) and stirring was continued at room temperature until no starting material was detected by TLC (50% ethyl acetate in hexane). The solvent was evaporated under reduced pressure and the residue was dissolved in CH2Cl2. The solution was cooled to 0° C. and triethylamine (60 μL, 0.43 mmol), HOBt.H2O (54 mg, 0.40 mmol), 6-(tert-butoxycarbonylamino)hexanoic acid (90 mg, 0.39 mmol) and DCC (80 mg, 0.39 mmol) were added. The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (10 mL) and the organic layer was washed with 10% citric acid and sat. aq NaHCO3, then it was dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (50% ethyl acetate in hexane) to give (±)-N-(6-(tert-butoxycarbonylamino)hexanoyl)-trans-3-(4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (201 mg, 84%): 1H NMR (300 MHz, CDCl3) δ 7.82 (dd, J=9, 3, 2H), 7.43 (t, J=8, 2H), 7.24 (t, J=7, 1H), 7.08 (m, 4H), 5.13 (br m, 1H, NH), 4.57 (br s, 1H, NH), 3.72-4.10 (m, 2H), 3.00-3.45 (m, 6H), 2.21 (t, J=7, 2H), 1.64 (m, 2H), 1.48 (m, 2H), 1.44 (s, 9H), 1.36 & 1.30 (s, 9H), 1.26 (m, 2H); HRMS (ESI) calculated for C31H45N3O6S2Na+ 642.2642. found 642.2654.

Workup

  1. customwas continued at room temperature until no starting material
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. stirringThe mixture was stirred at room temperature overnight
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate (10 mL)
  7. washthe organic layer was washed with 10% citric acid and sat. aq NaHCO3
  8. dry with materialit was dried over Na2SO4
  9. customevaporated
  10. customThe residue was purified by flash chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-95f7279c88f2490c8ad57ac9e1d8c3c9
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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