[(S*)-2-(3-Benzyloxy-phenyl)-1-((2S*,4R*)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester → [(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl ester

HRID 1432335Notes

Reaction equation

HRID 1432335 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([C@@H:24]1[CH2:28][C@@H:27]([CH3:29])[C:26](=[O:30])[O:25]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>C(N)CCC>[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1)[C@@H:24]([OH:25])[CH2:28][C@H:27]([C:26](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH3:29])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 11495571[(S*)-2-(3-Benzyloxy-phenyl)-1-((2S*,4R*)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 11648991[(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl esterYield 188.6%

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Conditions

Temperature
90 °C

Procedure

[(S*)-2-(3-Benzyloxy-phenyl)-1-((2S*,4R*)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester (4.0 g, 9.4 mmol) is dissolved in butylamine (200 ml) and stirred for 18 h in an heating bath of 90° C. The butylamine is evaporated and the residue is recrystallized from DCM/ether/hexane to give white crystals (4.42 g).

Workup

  1. customThe butylamine is evaporated
  2. customthe residue is recrystallized from DCM/ether/hexane

Sources & evidence

ORD record
ord-21f919459fd844af955ace2b14e4fcc9
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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