4-(trifluoromethyl)pyrimidine-5-carboxylic Acid → N-[[1-[4-(Methylsulfonyl)butyl]cyclobutyl]thioxomethyl]-4-[[[4-(trifluoromethyl)pyrimidin-5-yl]carbonyl]amino]-L-phenylalanine Methyl Ester

HRID 990145Notes

Reaction equation

HRID 990145 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][N:6]=[CH:5][N:4]=1.[CH3:14][O:15][C:16](=[O:41])[C@H:17]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1)[NH:18][C:19]([C:21]1([CH2:25][CH2:26][CH2:27][CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:24][CH2:23][CH2:22]1)=[S:20].COC(=O)[C@H](CC1C=CC(NC(C2C=NC(C(F)(F)F)=NC=2)=O)=CC=1)NC(C1(CCCCS(C)(=O)=O)CCC1)=S>>[CH3:14][O:15][C:16](=[O:41])[C@H:17]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:9]([C:8]2[C:3]([C:2]([F:1])([F:13])[F:12])=[N:4][CH:5]=[N:6][CH:7]=2)=[O:11])=[CH:36][CH:35]=1)[NH:18][C:19]([C:21]1([CH2:25][CH2:26][CH2:27][CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:22][CH2:23][CH2:24]1)=[S:20]

Participants

4

Reactant 3

HCID 116080754-(trifluoromethyl)pyrimidine-5-carboxylic AcidHCID 536517374-amino-N-[[1-[4-(methylsulfonyl)butyl]cyclobutyl]thioxomethyl)-L-phenylalanine methyl esterHCID 54401295N-[[1-[4-(methylsulfonyl)butyl]cyclobutyl]thioxomethyl]-4-[[[2-(trifluoromethyl) pyrimidin-5-yl]carbonyl]amino]-L-phenylalanine methyl ester

Product 1

HCID 12042617N-[[1-[4-(Methylsulfonyl)butyl]cyclobutyl]thioxomethyl]-4-[[[4-(trifluoromethyl)pyrimidin-5-yl]carbonyl]amino]-L-phenylalanine Methyl EsterYield 32%

Procedure

Using the general procedure described in example 45, starting with 4-(trifluoromethyl)pyrimidine-5-carboxylic acid and 4-amino-N-[[1-[4-(methylsulfonyl)butyl]cyclobutyl]thioxomethyl)-L-phenylalanine methyl ester, N-[[1-[4-(methylsulfonyl)butyl]cyclobutyl]thioxomethyl]-4-[[[2-(trifluoromethyl) pyrimidin-5-yl]carbonyl]amino]-L-phenylalanine methyl ester was prepared in 32% yield as an amorphous colorless solid. HR MS: Obs. mass, 601.1766. Calcd. mass, 601.1766 (M+H).

Workup

  1. customwas prepared in 32% yield as an amorphous colorless solid

Sources & evidence

ORD record
ord-49d952e4cd094551be3c147e7be7587c
Source dataset
uspto-grants-2002_10
Patent number
US06458844B2

Reaction notes

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