Aminoacetonitrile → (2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid cyanomethylamide

HRID 1009308Notes

Reaction equation

CN(C(O[N:9]1N=[N:16][C:11]2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([C@H:41]([NH:47][C@@H:48]([CH2:52][CH:53]([CH3:55])[CH3:54])[C:49]([OH:51])=O)[C:42]2[S:43][CH:44]=[CH:45][N:46]=2)=[CH:37][CH:36]=1.NCC#N>>[C:10]([CH2:11][NH:16][C:49](=[O:51])[C@@H:48]([NH:47][C@@H:41]([C:38]1[CH:37]=[CH:36][C:35]([Br:34])=[CH:40][CH:39]=1)[C:42]1[S:43][CH:44]=[CH:45][N:46]=1)[CH2:52][CH:53]([CH3:55])[CH3:54])#[N:9]

Participants

Reactant 4

HCID 10901Aminoacetonitrile

HCID 81531Diisopropylethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 67298316(2S)-2-{(S)-[(4-bromophenyl)thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid

Product 1

HCID 59715490(2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid cyanomethylamide

Procedure

In the presence of HATU (1 eq.) and diisopropylethylamine (4 eq.), (2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid was coupled with aminoacetonitrile (2 eq., 1 eq. excess) to give (2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid cyanomethylamide as a cream solid.

Sources & evidence

ORD record: ord-97625fb265e7447ea44f21a8ad60adfc
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973037B2

Reaction notes

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