(S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid → (S)-3-[[3-(8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenylcarbamoyl]-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1957998Notes

Reaction equation

HRID 1957998 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:19]=[C:20]([NH:28][C:29]2[N:38]=[CH:37][C:36]3[N:35]([CH3:39])[C:34](=[O:40])[CH2:33][N:32]([CH:41]([CH3:43])[CH3:42])[C:31]=3[N:30]=2)[CH:21]=[C:22]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:23]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][C:14](=[O:16])[NH:17][C:18]2[CH:23]=[C:22]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=[C:20]([NH:28][C:29]3[N:38]=[CH:37][C:36]4[N:35]([CH3:39])[C:34](=[O:40])[CH2:33][N:32]([CH:41]([CH3:43])[CH3:42])[C:31]=4[N:30]=3)[CH:19]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 1502098(S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acidHCID 592861742-(3-Amino-5-(methylsulfonyl)-phenylamino)-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one

Product 1

HCID 68423470(S)-3-[[3-(8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenylcarbamoyl]-methyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 82%

Procedure

The (S)-enantiomer was prepared with the same procedure used for the (R)-enantiomer and described in Scheme 12 starting from (S)-3-carboxymethyl-pyrrolidine-1-carboxylic acid tert butyl ester (132 mg; 0.576 mmol) and 2-(3-Amino-5-(methylsulfonyl)-phenylamino)-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one (150 mg; 0.384 mmol), 190 mg (0.316 mmol; 82% yield) of product were obtained.

Workup

  1. customThe (S)-enantiomer was prepared with the same procedure
  2. customwere obtained

Sources & evidence

ORD record
ord-4d0f6352a8324ba5860afcf894ffae47
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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