Boronic acid, cyclohexyl- (9CI) → HCID 54747898, compound

HRID 386757Notes

Reaction equation

HRID 386757 reaction equation
C1(B(O)O)CCCCC1.Br[C:11]1[CH:46]=[CH:45][CH:44]=[CH:43][C:12]=1[CH2:13][N:14]1[C:19](=[O:20])[C:18]([C:21]([NH:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:22])=[C:17]([OH:32])[C:16]2[CH2:33][N:34]([C:36]([C:38]3[N:39]=[CH:40][S:41][CH:42]=3)=[O:37])[CH2:35][C:15]1=2>>[CH2:13]([N:14]1[C:19](=[O:20])[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:22])=[C:17]([OH:32])[C:16]2[CH2:33][N:34]([C:36]([C:38]3[N:39]=[CH:40][S:41][CH:42]=3)=[O:37])[CH2:35][C:15]1=2)[C:12]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:11]=1

Participants

3

Reactant 2

HCID 199578Boronic acid, cyclohexyl- (9CI)HCID 66850684HCID 66850684, compound2×

Product 1

HCID 54747898HCID 54747898, compound

Procedure

In a failed attempt to couple cyclohexyl boronic acid with tert-butyl N-{[1-(2-bromobenzyl)-4-hydroxy-2-oxo-6-(1,3-thiazol-4-ylcarbonyl)-2,5,6,7-tetrahydro-1H-pyrrolo[3,4-b]pyridin-3-yl]carbonyl}glycinate (prepared in similar fashion to Intermediate 5), and using a similar procedure to that described in Example 49 Step A, the above side product, compound E54-1 obtained. HPLC/MS: 454.9 (M+1); Rt=2.67 min.

Workup

  1. customthe above side product, compound E54-1 obtained

Sources & evidence

ORD record
ord-1891e245d9194f0cbaf4f3a397437a1f
Source dataset
uspto-grants-2013_02
Patent number
US08372863B2

Reaction notes

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