Hydrochloric Acid → phenylmethyl [(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]carbamate hydrochloride

HRID 852573Notes

Reaction equation

HRID 852573 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[NH:10][CH2:11][C@@H:12]([OH:29])[C@@H:13]([NH:21]C(OC(C)(C)C)=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31].O1CCOCC1>C1COCC1>[ClH:31].[CH2:1]([O:8][C:9](=[O:30])[NH:10][CH2:11][C@@H:12]([OH:29])[C@@H:13]([NH2:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 21356811((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester

Product 1

HCID 69358558phenylmethyl [(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]carbamate hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester (D103) (31.5 g, 76.1 mmol, 1 equiv) in THF (300 ml) was treated with 4N HCl solution in dioxan (40 ml, 160 mmol, 2.1 equiv). The resulting solution was stirred at room temperature for 2 h then concentrated in vacuo. The residue was triturated with Et2O/iso-hexane to give ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester hydrochloride (D104) (22.1 g, 83%) as a white solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated with Et2O/iso-hexane

Sources & evidence

ORD record
ord-b3f6342c7c704f84a92f21de8be72edc
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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