Methyl bromoacetate → (2R)-2-(BOC)amino-N-{3-[cyclohexyl(methoxycarbonyl)amino]azetidine-1-yl}-3-(4-chlorophenyl)propionamide

HRID 1670033Notes

Reaction equation

HRID 1670033 reaction equation
CS(N(C1C=CC(Cl)=CC=1)[C@@H](C(O)=O)C)(=O)=O.[C:18]([NH:25][C@H:26]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)[C:27]([NH:29][N:30]1[CH2:33][CH:32]([NH:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH2:31]1)=[O:28])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].BrC[C:51]([O:53][CH3:54])=[O:52]>>[C:18]([NH:25][C@H:26]([CH2:41][C:42]1[CH:43]=[CH:44][C:45]([Cl:48])=[CH:46][CH:47]=1)[C:27]([NH:29][N:30]1[CH2:31][CH:32]([N:34]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:51]([O:53][CH3:54])=[O:52])[CH2:33]1)=[O:28])([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19]

Participants

4

Reactant 3

HCID 60984Methyl bromoacetateHCID 967528(2R)-N-methanesulfonyl-(4-chlorophenyl)alanineHCID 67342965(2R)-2-(BOC)amino-N-[3-(cyclohexylamino)azetidine-1-yl]-3-(4-chlorophenyl)propionamide2×

Product 1

HCID 67344148(2R)-2-(BOC)amino-N-{3-[cyclohexyl(methoxycarbonyl)amino]azetidine-1-yl}-3-(4-chlorophenyl)propionamide

Procedure

The title compound was prepared following the procedure described in Step A of Intermediate 135 using (2R)-2-(BOC)amino-N-[3-(cyclohexylamino)azetidine-1-yl]-3-(4-chlorophenyl)propionamide prepared in Intermediate 202 and methyl bromoacetate.

Sources & evidence

ORD record
ord-e88700549a0548c1b65a1ce912b3f602
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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