Methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride → Methyl (2S,4R)-1-{[(3-Chloro-4-cyano-2-methylphenyl)amino]-carbonyl}-4-hydroxypyrrolidine-2-carboxylate

HRID 751116Notes

Reaction equation

HRID 751116 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:10][CH:9]([OH:11])[CH2:8][NH:7]1)=[O:5].[Cl:12][C:13]1[C:20]([CH3:21])=[C:19]([N:22]=[C:23]=[O:24])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>>[Cl:12][C:13]1[C:20]([CH3:21])=[C:19]([NH:22][C:23]([N:7]2[CH2:8][C@H:9]([OH:11])[CH2:10][C@H:6]2[C:4]([O:3][CH3:2])=[O:5])=[O:24])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 16242427Methyl 4-hydroxypyrrolidine-2-carboxylate hydrochlorideHCID 167318492-Chloro-4-isocyanato-3-methylbenzonitrile

Product 1

HCID 59754306Methyl (2S,4R)-1-{[(3-Chloro-4-cyano-2-methylphenyl)amino]-carbonyl}-4-hydroxypyrrolidine-2-carboxylate

Procedure

The title compound was prepared from compound 56A (300 mg, 1.65 mmol) and isocyanate 23E (312 mg, 1.62 mmol) by procedures analogous to that described for Example 55A to afford a white foam (375.6 mg, 69%). HPLC: 1.68 min (retention time) (Conditions: YMC S-5 C-18 (4.6×250 mm), eluting with 0-100% B, 4 min gradient. (A=90% H2O—10% CH3CN—0.1% TFA and B=10% H2O—90% CH3CN—0.1% TFA); Flow rate at 4 mL/min. UV detection at 220 nm. Chiral HPLC: retention time=12.92 min (98.9%); Conditions: AD (4.6×250 mm); Eluted with 20% isopropanol in heptane for 30 min at 1 mL/min. MS (ES) m/z 338 [M+H]+.

Sources & evidence

ORD record
ord-1034020d23f443cbb49eb8642a862fda
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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