Triethylamine → HCID 67233944, compound

HRID 1952440Notes

Reaction equation

HRID 1952440 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:9]1)([O:3]C(C)(C)C)=[O:2].C(OCC)(=O)C.C(N(CC)CC)C.[CH:44]1[CH:49]=[CH:48][C:47]([CH2:50]OC(Cl)=O)=[CH:46][CH:45]=1>FC(F)(F)C(O)=O.CCCCCC>[C:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([NH:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:9]1)([O:3][CH2:50][C:47]1[CH:48]=[CH:49][CH:44]=[CH:45][CH:46]=1)=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 67232863HCID 67232863, compound

Product 1

HCID 67233944HCID 67233944, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

(3R,4R)—N-Boc-3-(4-Phenoxybenzenesulfonamido)-4-hydroxy-pyrrolidine (100 mg, 0.23 mmol) was dissolved in trifluoroacetic acid (1 mL) and was stirred until no starting material was detected on TLC (50% ethyl acetate in hexane). The reaction mixture was evaporated under reduced pressure and the residue was dissolved in CH2Cl2 (2 mL). The solution was cooled to 0° C. and triethylamine (71 μL, 0.84 mmol) and Cbz-Cl (41 mg, 0.24 mmol) were added, and the mixture was stirred for 2 hr at room temperature. The solution was washed with water, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (25% ethyl acetate in hexane) to give (3R,4R)—N-Cbz-3-(4-phenoxybenzenesulfonamido)-4-hydroxypyrrolidine (100 mg, 93%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=9, 2H), 7.42 (t, J=8, 2H), 7.34 (m, 5H), 7.24 (t, J=7, 1H), 7.08 (m, 4H), 5.10 (s, 2H), 4.85 & 4.76 (br s, 1H), 4.34 & 4.26 (br m, 1H), 3.72 (m, 2H), 3.55 (br m, 1H), 3.32 & 3.19 (m, 2H), 2.65 & 2.53 (br s, 1H); [°]20D=−29.5° (c=0.8, CHCl3).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2 (2 mL)
  3. stirringthe mixture was stirred for 2 hr at room temperature
  4. washThe solution was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9d97feca9b594efda824e3ccaf88d7e1
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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