Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 1-[6-(Benzyloxy)pyridin-3-yl]cyclopropanecarboxylic acid

HRID 969120Notes

Reaction equation

HRID 969120 reaction equation
F[P-](F)(F)(F)(F)F.N1([O:17][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:28]([O:35][C:36]1[N:41]=[CH:40][C:39]([C:42]2([C:45](N3CC[C@@]4(C5C=CC=CC=5C(=O)O4)C3)=[O:46])[CH2:44][CH2:43]2)=[CH:38][CH:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:36]1[N:41]=[CH:40][C:39]([C:42]2([C:45]([OH:46])=[O:17])[CH2:43][CH2:44]2)=[CH:38][CH:37]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66662157(1r)-1'-({1-[6-(Benzyloxy)pyridin-3-yl]cyclopropyl}carbonyl)-3h-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Product 1

HCID 666616601-[6-(Benzyloxy)pyridin-3-yl]cyclopropanecarboxylic acid

Procedure

Following the BOP coupling the desired product, (1R)-1′-({1-[6-(benzyloxy)pyridin-3-yl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one, was purified by prep-HPLC. LC/MS: 441.2 (M+H+).

Sources & evidence

ORD record
ord-bd7c67851cb745669275abb961721f8b
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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