Succinimide → N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(succinimidomethyl)phenyl]-L-phenylalanine tert-butyl ester

HRID 24695

Reaction equation

HRID 24695 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18](=[O:50])[C@H:19]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[C:43]([O:44][CH3:45])=[CH:42][C:41]([CH2:46]O)=[CH:40][C:39]=2[O:48][CH3:49])=[CH:34][CH:33]=1)[NH:20][C:21](=[O:30])[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:70]1(=[O:76])[NH:74][C:73](=[O:75])[CH2:72][CH2:71]1>C1COCC1>[C:13]([O:17][C:18](=[O:50])[C@H:19]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[C:39]([O:48][CH3:49])=[CH:40][C:41]([CH2:46][N:74]3[C:73](=[O:75])[CH2:72][CH2:71][C:70]3=[O:76])=[CH:42][C:43]=2[O:44][CH3:45])=[CH:34][CH:33]=1)[NH:20][C:21](=[O:30])[C:22]1[C:23]([Cl:29])=[CH:24][CH:25]=[CH:26][C:27]=1[Cl:28])([CH3:15])([CH3:16])[CH3:14]

Participants

6

Reactant 4

HCID 11439SuccinimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 54401991N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(hydroxymethyl)phenyl]-L-phenylalanine tert-butyl ester

Product 1

HCID 22970625N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(succinimidomethyl)phenyl]-L-phenylalanine tert-butyl esterYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

DEAD (0.13 mL) was added to an ice-cooled solution of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(hydroxymethyl)phenyl]-L-phenylalanine tert-butyl ester (250 mg), triphenylphosphine (175 mg) and succinimide (90 mg) in THF (3 mL) under N. The mixture was stirred at 0° C. for 30 min, and warmed to room temperature and stirred for 2 h. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was extracted with EtOAC. The combined organic layer was dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1:1) to give N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(succinimidomethyl)phenyl]-L-phenylalanine tert-butyl ester (138 mg).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 2 h
  3. customThe mixture was partitioned between H2O and EtOAc
  4. extractionthe aqueous layer was extracted with EtOAC
  5. dry with materialThe combined organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1:1)

Sources & evidence

ORD record
ord-56c872874e3840c7b4386e443eca2318
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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