Dimethylformamide → Z-Ala-OMe

HRID 1450726Notes

Reaction equation

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

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 736104N-carbobenzyloxyalanine

Product 1

HCID 6993447Z-Ala-OMeYield 92.8%

Procedure

CBZ-Ala (10, 0.165 g, 0.74 mmol) was added to 6 mL of dry DMF containing 1.1 g (500 mol % ) of 2 (R=Me) and the reaction mixture was stirred at 16 h a t room temperature. Following the general procedure gave 0.163 g of 19, 93%, as an oil: [α]25D -32.7° (c 1.3, MeOH) [Lit14 [α]25D -33.0° (c 1.0, MeOH )]; IR 3340, 3060, 3030, 1720; 1H NMR δ 7.34-7.26 (m, 5H), 5.53 (d, 1H, J=5.9), 5.10 (s, 2H), 4.39 (t, 1H, J=7.3), 3.73 (s, 3H), 1.40 (d, 3H, J=7.2).

Sources & evidence

ORD record: ord-e01a71d3c6c04d4ea3a01d09e2811283
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05602264

Reaction notes

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