HCID 90054447, compound → (R)-methyl 4-(2-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)ethyl)benzoate

HRID 709097Notes

Reaction equation

HRID 709097 reaction equation
[F:1][C:2]1([F:22])[CH2:6][C@H:5]([CH2:7][OH:8])[N:4]([CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:3]1=[O:21].FC1(F)C[C@H](CO)N(CCCCCCC(OC)=O)C1=O>ClCCl.CO>[F:22][C:2]1([F:1])[CH2:6][C@H:5]([CH:7]=[O:8])[N:4]([CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:3]1=[O:21]

Participants

4

Reactant 2

HCID 90054447HCID 90054447, compoundHCID 90054523(R)-methyl 7-(3,3-difluoro-5-(hydroxymethyl)-2-oxopyrrolidin-1-yl)heptanoate

Product 1

HCID 90054501(R)-methyl 4-(2-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)ethyl)benzoate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

(R)-methyl 4-(2-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)ethyl)benzoate was prepared from 12b using the oxidation procedure (Step K) described for the preparation of intermediate 13a from intermediate 12a; TLC Rf 0.4 (solvent system: 95:5 v/v dichloromethane-methanol); 1H-NMR (CDCl3) δ 9.2 (s, 1H), 7.9 (dd, 2H), 7.24 (dd, 2H), 3.98-3.91 (m, 1H), 3.87 (s, 3H), 3.74-3.48 (m, 2H), 3.51-3.46 (m, 2H), 3.1-2.8 (m, 2H), 2.48-2.22 (m, 2H).

Sources & evidence

ORD record
ord-8c4180296f1c47ce899ff31c616967c8
Source dataset
uspto-grants-2015_11
Patent number
US09180116B2

Reaction notes

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