Ethanol → N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-beta-alanine

HRID 1934394Notes

Reaction equation

HRID 1934394 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:46])[CH2:6][C@@H:7]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1)[NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:33])/[CH:18]=[CH:19]/[CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH2:12]1)=[O:10].CCO>O.O1CCCC1>[C:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][CH:20](/[CH:19]=[CH:18]/[C:17]([N:13]2[CH2:14][CH2:15][CH2:16][C@@H:11]([C:9]([NH:8][C@H:7]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=3)[CH2:6][C:5]([OH:46])=[O:4])=[O:10])[CH2:12]2)=[O:33])[CH2:21][CH2:22]1)=[O:27])([CH3:31])([CH3:30])[CH3:32]

Participants

6

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 86758030N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-beta-alanine methyl ester

Product 1

HCID 86758032N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-beta-alanineYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (0.11 g) in H2O (10 ml) was added to a solution of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-β-alanine methyl ester (1.83 g) in tetrahydrofuran (10 ml)-EtOH (10 ml) at 0° C. The reaction mixture was stirred for 3 hours at room temperature, and the solvent was evaporated in vacuo. The residue was resolved in ethyl acetate-water, and acidified with 10% aq. KHSO4. The whole was washed with water and brine, dried over MgSO4, and evaporated in vacuo to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-β-alanine as a colorless oil (1.33 g, 74.4%).

Workup

  1. customthe solvent was evaporated in vacuo
  2. washThe whole was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8276d25a2e444037bdc1606f08a323d1
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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