(R)-3-((tert-butoxycarbonyl)amino)butanoic acid → tert-Butyl(R)-4-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxobutan-2-ylcarbamate

HRID 1888111Notes

Reaction equation

HRID 1888111 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[C:17]([NH:24][C@@H:25]([CH2:27][C:28](O)=[O:29])[CH3:26])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][N:11]([C:28](=[O:29])[CH2:27][C@H:25]([NH:24][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH3:26])[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2761507(R)-3-((tert-butoxycarbonyl)amino)butanoic acidHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

Product 1

HCID 59444245tert-Butyl(R)-4-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxobutan-2-ylcarbamate

Procedure

tert-Butyl(R)-4-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxobutan-2-ylcarbamate was prepared from (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol and Boc-D-beta-homoalanine using the conditions described in Example 1, Step 2. MS (ESI+)=425.1 (M+H)+.

Sources & evidence

ORD record
ord-0a9617b836ba4f8d97437b95874f3181
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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