Boc-L-methionine → HCID 69492394, compound

HRID 1768148Notes

Reaction equation

HRID 1768148 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:17][C:18]1[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=1)[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:14](=[O:16])[NH:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][C:20]2[CH:30]=[CH:31][CH:32]=[C:18]([F:17])[CH:19]=2)=[CH:28][CH:27]=1)[CH2:10][CH2:11][S:12][CH3:13])([CH3:5])([CH3:6])[CH3:7]

Participants

4

Reactant 3

HCID 89857Boc-L-methionineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167753144-(3-Fluoro-benzyloxy)-phenylamine

Product 1

HCID 69492394HCID 69492394, compound

Procedure

Condensation of (S)-BOC-methionine and 4-(3-fluorobenzyloxy)-phenylamine [Example 3b)] by HBTU yields the (S)-{1-[4-(3-fluoro-benzyloxy)-phenylcarbamoyl]-3-methylsulfanyl-propyl}-carbamic acid tert-butyl ester as a light yellow solid; MS: m/e=449 (M+H)+. The following methylation and cyclisation yields the (S)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid tert-butyl ester as a white solid; MS: m/e=401 (M+H)+. The cleavage of the BOC-group yields the (S)-3-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride as a white solid; MS: m/e=301 (M+H)+.

Sources & evidence

ORD record
ord-f2bb9093885e424db29c3cfe24a8bce8
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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