Water → HCID 57970206, compound

HRID 1666672Notes

Reaction equation

HRID 1666672 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:16]([OH:17])[CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].O>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:16]([O:17][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57970216HCID 57970216, compound

Product 1

HCID 57970206HCID 57970206, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

t-Butyl (3R,4S)-3-benzyloxycarbonylamino-4-hydroxypyrrolidine-1-carboxylate (38 g) was dissolved in chloroform (380 mL), and the mixture was ice-cooled, followed by addition of triethylamine (22 mL) and methanesulfonylchloride (11 mL). The mixture was stirred for 2 h with ice cooling, and water was added to separate the layers. The organic layer was washed with water, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain crude t-butyl (3R,4S)-3-benzyloxycarbonylamino-4-methanesulfonyloxypyrrolidine-1-carboxylate. This compound was used in the subsequent step without purification.

Workup

  1. temperaturecooled
  2. additionwas added
  3. customto separate the layers
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1de59791372b42f99d0f872dcc5cafc9
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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