Diisopropylethylamine → (1R)-1'-({1-[4-(2-Amino-1,3-thiazol-4-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 969111Notes

Reaction equation

HRID 969111 reaction equation
C(N(CC)C(C)C)(C)C.[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3([C:25]([OH:27])=O)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:15]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[NH:43]1[CH2:47][CH2:46][C:45]2([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=3[C:49](=[O:56])[O:48]2)[CH2:44]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3([C:25]([N:43]4[CH2:47][CH2:46][C@@:45]5([C:51]6[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=6[C:49](=[O:56])[O:48]5)[CH2:44]4)=[O:27])[CH2:23][CH2:24]3)=[CH:20][CH:21]=2)[N:15]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86602277[4-(2-Amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylic acidHCID 86602279(1S)-(+)-10-camphorsulfonic acid 3H-spiro-[2-benzofuran-1,3'-pyrrolidin]-3-one

Product 1

HCID 86602278(1R)-1'-({1-[4-(2-Amino-1,3-thiazol-4-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (50 μL, 0.3 mmol) was added to a mixture of -[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylic acid (26.0 mg, 0.1 mmol), (1S)-(+)-10-camphorsulfonic acid-3H-spiro-[2-benzofuran-1,3′-pyrrolidin]-3-one (1:1) (42.1 mg, 0.01 mmol) and BOP (57.0 mg, 0.13 mmol) in DMF (0.5 mL) at room temperature, and the reaction mixture was stirred for about 5 hours (the completion of the reaction was determined by HPLC). The crude product was purified by prep-HPLC. LC-MS: 432.1 (M+H)+.

Workup

  1. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-1df13ee71495405cacbbc70f5e83391f
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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