Succinic anhydride → 3-(1,5-Di(t-butoxycarbonyl)-3-(2-(t-butoxycarbonyl)ethyl)pentan-3-ylcarbamoyl)propanoic acid

HRID 1397123Notes

Reaction equation

HRID 1397123 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]([NH2:29])([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]([NH:29][C:30]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:36])([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 10927842Aminotriester

Product 1

HCID 866665363-(1,5-Di(t-butoxycarbonyl)-3-(2-(t-butoxycarbonyl)ethyl)pentan-3-ylcarbamoyl)propanoic acidYield 64.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of amine 72 (513 mg, 1.23 mmol) in CH2Cl2 (6.2 mL) was added succinic anhydride (135 mg, 1.35 mmol) and DMAP (8 mg, 0.062 mmol). The mixture was stirred for 6 h 15 min and concentrated to dryness. The crude product was purified by flash chromatography on a Biotage™ flash chromatography system, using a gradient of 50-100% EtOAc in CH2Cl2 as eluent to yield acid 73 (407 mg, 64%) as a white foam: 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 27H), 1.97-2.01 (m, 6H), 2.23-2.26 (m, 6H), 2.47-2.51 (m, 2H), 2.65-2.68 (m, 2H), 6.83 (s, 1H).

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude product was purified by flash chromatography on a Biotage™ flash chromatography system

Sources & evidence

ORD record
ord-21a9f2f9aa6e4bac9c5ef545a37669a5
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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