Hydrochloric Acid → HCID 86654493, compound

HRID 1952435Notes

Reaction equation

HRID 1952435 reaction equation
Cl.C([N:9]1[CH2:13][C@@H:12]([S:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:11]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:10]1)(OC(C)(C)C)=O.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.O.[C:53]([O:57][C:58]([NH:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][C:66](O)=[O:67])=[O:59])([CH3:56])([CH3:55])[CH3:54].C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C>[C:53]([O:57][C:58]([NH:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][C:66]([N:9]1[CH2:13][C@@H:12]([S:14][C:15]([CH3:17])([CH3:18])[CH3:16])[C@H:11]([NH:19][S:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH2:10]1)=[O:67])=[O:59])([CH3:56])([CH3:55])[CH3:54]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 86654494HCID 86654494, compound

Product 1

HCID 86654493HCID 86654493, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1.5 M HCl in ethyl acetate (1 mL) was added (±)-N-Boc-trans-3-(4-phenylbenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (220 mg, 0.45 mmol) and the mixture was stirred until no starting material could be detected by TLC (50% ethyl acetate). The solvent was evaporated under reduced pressure and the residue was dissolved in CH2Cl2 (2 mL) and cooled to 0° C. To the solution was added triethylamine (69 μL, 0.50 mmol), HOBt.H2O (61 mg, 0.45 mmol), and 6-(tert-butoxy-carbonylamino)hexanoic acid (104 mg, 0.39 mmol) and DCC (92 mg, 0.45 mmol). The mixture was stirred overnight, then it was concentrated under reduced pressure. 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-phenylbenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (220 mg, 81%): 1H NMR (300 MHz, CDCl3) δ 7.94 (dd, J=9, 4, 2H), 7.75 (t, J=8, 2H), 7.61 (m, 2H), 7.46 (m, 3H), 5.21 (br s, 1H, NH), 4.56 (br s, 1H, NH), 3.77-4.11 (m, 2H), 3.02-3.49 (m, 6H), 2.22 (t, J=7, 2H), 1.63 (m, 2H), 1.49 (m, 2H), 1.44 (s, 9H), 1.36 & 1.29 (s, 9H), 1.25 (m, 2H); HRMS (ESI) calculated for C31H45N3O5S2Na+ 626.2698. found 626.2699.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2 (2 mL)
  3. stirringThe mixture was stirred overnight
  4. concentrationit was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  6. washthe organic layer was washed with 10% citric acid and sat. aq NaHCO3
  7. dry with materialit was dried over Na2SO4
  8. customevaporated
  9. customThe residue was purified by flash chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ac147bc8fd9c43e4bea054ad69406439
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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