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

HRID 1771160Notes

Reaction equation

HRID 1771160 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-79bedf261bf8412f87aa039514b9c9ac
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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