p-Toluenesulfonic acid → tert-butyl (S)-1-hydroxy-3-((R)-oxepan-3-yl)propan-2-ylcarbamate

HRID 451830Notes

Reaction equation

HRID 451830 reaction equation
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH2:14][C@H:15]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17][CH2:16]2)[CH2:4][O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1>CO.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>[OH:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[CH2:14][C@H:15]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17][CH2:16]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59201664(S)-tert-butyl 2,2-dimethyl-4-((R)-oxepan-3-ylmethyl)oxazolidine-3-carboxylate

Product 1

HCID 59201534tert-butyl (S)-1-hydroxy-3-((R)-oxepan-3-yl)propan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 90495Di-tert-butyl dicarbonateCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 2,2-dimethyl-4-((R)-oxepan-3-ylmethyl)oxazolidine-3-carboxylate (160 mg, 0.51 mmol) in MeOH (10 mL) was added p-TSA (30 mg, 0.17 mmol) and stirred at rt for 2 h. TEA (1 mL) was added, followed by 1 drop of Boc2O. The reaction mixture was stirred for another 30 min. The solvent was removed under vacuum to give crude product tert-butyl (S)-1-hydroxy-3-((R)-oxepan-3-yl)propan-2-ylcarbamate, which was used for next step without further purification. MS ESI +ve m/z 296 (M+Na).

Workup

  1. stirringThe reaction mixture was stirred for another 30 min
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0424ef51782941a38368951d9d2f393d
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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