(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid → 2-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-cyclopropyl-2-oxo-2-pyrrolidin-1-yl-ethyl)-amide

HRID 1898500Notes

Reaction equation

HRID 1898500 reaction equation
CC(O[C:6]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH:10]1[CH2:12][CH2:11]1)=[O:7])(C)C.[C:16]([NH:23][C@@H:24](C(O)=O)[C:25]([CH3:28])(C)C)(OC(C)(C)C)=O.[CH2:32]([N:34]1[CH:38]=[C:37]([C:39]2[N:44]=[C:43]3[C:45](C(O)=O)=[CH:46][N:47](COCC[Si](C)(C)C)[C:42]3=[N:41][CH:40]=2)[CH:36]=[N:35]1)[CH3:33]>>[CH:10]1([C@@H:9]([NH:8][C:6]([C:45]2[C:43]3[C:42](=[N:41][CH:40]=[C:39]([C:37]4[CH:36]=[N:35][N:34]([CH2:32][CH3:33])[CH:38]=4)[N:44]=3)[NH:47][CH:46]=2)=[O:7])[C:13](=[O:15])[N:23]2[CH2:16][CH2:28][CH2:25][CH2:24]2)[CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 584385442-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

Product 1

HCID 533859872-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-cyclopropyl-2-oxo-2-pyrrolidin-1-yl-ethyl)-amide

Procedure

Prepared according to the procedure outlined in Example 1 substituting Boc-D-cyclopropyl glycine for Boc-D-tert-leucine and 2-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid for 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2, 3-1)]pyrazine-7-carboxylic acid. MS: (M+H)+=408; mp=210.0-212.0.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4ebac12158904356a8c7022b99e884f9
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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