Methanol → Methyl (R)-3-[(benzyloxycarbonyl)amino]-4-hydroxybutanoate

HRID 1476259

Reaction equation

HRID 1476259 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][C@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:25][OH:26]>>[CH2:10]([O:9][C:8]([NH:7][C@@H:4]([CH2:25][OH:26])[CH2:3][C:2]([O:6][CH3:5])=[O:1])=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate2×

Product 1

HCID 59108917Methyl (R)-3-[(benzyloxycarbonyl)amino]-4-hydroxybutanoate

Procedure

(R)-Benzyl 5-oxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 3, 27.0 g, 114.78 mmol) was dissolved in methanol (75 ml) and triethylamine (75 ml) was added at room temperature. The resulting mixture was allowed to stir overnight at this temperature. The mixture was concentrated in vacuo to provide the title product. This material was used to prepare INTERMEDIATE 5 without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c3d0e1f542754747bcf0c167079150c7
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Linked notes

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