Methylamine → 5-Oxo-pyrrolidine-3-carboxylic acid methylamide

HRID 1244584Notes

Reaction equation

[O:1]=[C:2]1[NH:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3]1.CN.[CH3:12][N:13](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:12][NH:13][C:7]([CH:4]1[CH2:3][C:2](=[O:1])[NH:6][CH2:5]1)=[O:9]

Participants

Reactant 3

HCID 6329Methylamine

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 167851365-Oxopyrrolidine-3-carboxylic acid

Product 1

HCID 552206635-Oxo-pyrrolidine-3-carboxylic acid methylamide

Procedure

In an analogous manner to that described in Example 24f, by condensing (S)-1-(4-benzyloxy)-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid with methylamine using HBTU as the condensation agent there is obtained (S)-1-(4-benzyloxy)-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methylamide as a white solid. MS: m/e=325 (M+H)+; [α]589=+32.02° (c=1.037, CH2Cl2).

Sources & evidence

ORD record: ord-241c57075339411e93f7586d66a8a076
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122562B2

Reaction notes

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