Methanol → (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane

HRID 375229Notes

Reaction equation

HRID 375229 reaction equation
[NH2:1][C@H:2]([C@@H:10]([OH:21])[CH2:11][C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C([N+]([O-])=O)=CC=C([O:31][C:32]([O:34][CH2:35][C:36]2[S:40][CH:39]=[N:38][CH:37]=2)=[O:33])C=1.CO.C(N)(C)C>C1COCC1.C(Cl)(Cl)Cl>[NH2:20][C@@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][C@H:10]([OH:21])[C@@H:2]([NH:1][C:32]([O:34][CH2:35][C:36]1[S:40][CH:39]=[N:38][CH:37]=1)=[O:31])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:1][C@H:2]([C@@H:10]([OH:21])[CH2:11][C@@H:12]([NH:20][C:32]([O:34][CH2:35][C:36]1[S:40][CH:39]=[N:38][CH:37]=1)=[O:33])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateHCID 10085299(2S,3S,5S)-2,5-Diamino-1,6-diphenylhexan-3-OL

Product 2

HCID 10812314(2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexaneYield 28%HCID 111019781,3-Thiazol-5-ylmethyl N-((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl)carbamateYield 16%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 500 mg (1.76 mmol) of (2S,3S,5S)-2,5-diamino-1,6-diphenyl-3-hydroxyhexane and 480 mg (1.71 mmol) of ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate in 20 ml of THF was stirred at ambient temperature for 4 h. After removal of the solvent in vacuo, the residue was purified by silica gel chromatography using first 2% then 5% methanol in chloroform to provide a mixture of the two desired compounds. Silica gel chromatography of the mixture using a gradient of 0-1-2% methanol in 93:2 isopropylamine: chloroform provided 110 mg (16%) of (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane (Rf 0.48, 96:2:2 chloroform:methanol:isopropylamine) and 185 mg (28%) of (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane (Rf 0.44, 96:2:2 chloroform:methanol:isopropylamine).

Workup

  1. customAfter removal of the solvent in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. custom5% methanol in chloroform to provide
  4. additiona mixture of the two desired compounds

Sources & evidence

ORD record
ord-dfce1ce5589a4488928b0b650e229dd9
Source dataset
uspto-grants-1996_01
Patent number
US05484801

Reaction notes

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