Succinic anhydride → HCID 59916552, compound

HRID 993146Notes

Reaction equation

HRID 993146 reaction equation
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:17][C@H:16]2[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][N:9]1[CH2:18][C@@H:19]([OH:48])[C@@H:20]([NH:28][C:29](=[O:47])[C@H:30]([C:40]([S:43]([CH3:46])(=[O:45])=[O:44])([CH3:42])[CH3:41])[NH:31][C:32]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)=[O:33])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:49]1(=[O:55])[O:54][C:52](=[O:53])[CH2:51][CH2:50]1>O1CCCC1>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:17][C@H:16]2[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][N:9]1[CH2:18][C@@H:19]([O:48][C:49](=[O:55])[CH2:50][CH2:51][C:52]([OH:54])=[O:53])[C@@H:20]([NH:28][C:29](=[O:47])[C@H:30]([C:40]([S:43]([CH3:46])(=[O:45])=[O:44])([CH3:42])[CH3:41])[NH:31][C:32]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)=[O:33])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 10212034HCID 10212034, compound

Product 1

HCID 59916552HCID 59916552, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 68 mg (0.1 mmol) of N-tert-butyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydro-2-[2(R)-hydroxy-3(S)-[[3-(methanesulfonyl)-N-[(3-pyridyl)carbonyl]-L-valyl]amino]-4-phenylbutyl]-3(S)-isoquinolinecarboxamide (example 7) in 10 ml of tetrahydrofuran was treated with 10 mg (1 mmol) of succinic anhydride (Aldrich 23,960-0) and heated at reflux overnight. The volatiles were evaporated under reduced pressure and the residue chromatographed on silica eluting with dichloromethane/methanol (19:1) to give 53 mg of N-tert-butyl-2-[2(R)-(3-carboxypropionyloxy)-3(S)-[[3-(methanesulfonyl)-N-[(3-pyridyl)carbonyl]-L-valyl]amino]-4-phenylbutyl]-1,2,3,4,4a(S),5,6,7,8,8a(S)decahydro-3(S)-isoquinolinecarboxamide as a foam, [M+H]+ 784.5.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe volatiles were evaporated under reduced pressure
  4. customthe residue chromatographed on silica eluting with dichloromethane/methanol (19:1)

Sources & evidence

ORD record
ord-62e03e83d4604dc8bbec230bab972b04
Source dataset
uspto-grants-2002_10
Patent number
US06472404B1

Reaction notes

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