Ammonium Hydroxide → tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate

HRID 660385Notes

Reaction equation

HRID 660385 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([CH:24]([CH3:26])[CH3:25])[CH2:11][C@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@@H:13]1[CH2:15][O:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:27].[OH-]>CO>[NH2:27][CH2:15][C@H:13]([OH:14])[C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86649362HCID 86649362, compound

Product 1

HCID 59630993tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamateYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (1S,3S)-3-(benzyloxymethyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate (500 mg, 1.38 mmol) in MeOH (5 mL), was added NH4OH (5 mL). The mixture was stirred at rt for 18 h. The mixture was concentrated in vacuo to give tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate (510 mg, 97.3%). 1H NMR (400 MHz, CD3OD): 0.86 (m, 6H), 1.41 (s, 12H), 1.82 (brs, 1H), 2.50 (m, 1H), 3.42 (m, 2H), 3.61 (m, 2H), 3.71 (m, 3H), 3.90 (m, 4H), 6.61 (m, 1H), 7.31 (m, 5H), 7.71 (m, 1H); MS: 381 (M++1)

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-547a06b058af479abdf3ca4a956ea12e
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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