Benzyl (4R)-4-hydroxy-L-prolinate--hydrogen chloride (1/1) → (2S-trans)-N-[4-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]pyrimidin-2-yl]-4-hydroxy-2-pyrrolidinecarboxylic acid, phenylmethyl ester

HRID 1871979Notes

Reaction equation

HRID 1871979 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:17])[C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:19]1[N:24]=[C:23]([N:25]2[CH:30]=[C:29]([CH:31]3[C:37]4[CH:38]=[CH:39][C:40]([CH3:42])=[CH:41][C:36]=4[CH:35]=[CH:34][C:33]4[CH:43]=[C:44]([CH3:47])[CH:45]=[CH:46][C:32]3=4)[C:28](=[O:48])[NH:27][C:26]2=[O:49])[CH:22]=[CH:21][N:20]=1>>[CH3:42][C:40]1[CH:39]=[CH:38][C:37]2[CH:31]([C:29]3[C:28](=[O:48])[NH:27][C:26](=[O:49])[N:25]([C:23]4[CH:22]=[CH:21][N:20]=[C:19]([N:12]5[CH2:13][C@H:14]([OH:16])[CH2:15][C@H:11]5[C:10]([O:9][CH2:2][C:3]5[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=5)=[O:17])[N:24]=4)[CH:30]=3)[C:32]3[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][C:33]=3[CH:34]=[CH:35][C:36]=2[CH:41]=1

Participants

3

Reactant 2

HCID 16212860Benzyl (4R)-4-hydroxy-L-prolinate--hydrogen chloride (1/1)HCID 186897501-[2-Chloropyrimidin-4-yl}-5-[2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 86755653(2S-trans)-N-[4-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]pyrimidin-2-yl]-4-hydroxy-2-pyrrolidinecarboxylic acid, phenylmethyl ester

Procedure

The subtitle compound was prepared from trans-4-hydroxy-L-proline benzyl ester hydrochloride (0.928 g) and the product of example 8 step (ii) (0.3 g) by the method of example 10 step (ii). Purification was by chromatography eluting with 50-60% ethyl acetate in isohexane. Yield 0.29 g.

Workup

  1. customPurification
  2. washeluting with 50-60% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-4134fa5a93ab4867bb635838b11dc9fa
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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