Fmoc-Asp(OAll)-OH → HCID 10529786, compound

HRID 1482264Notes

Reaction equation

HRID 1482264 reaction equation
ClC(Cl)(Cl)C(=N)O[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[CH:17]1[C:29]2[CH:28]([CH2:30][O:31][C:32]([NH:34][C@@H:35]([CH2:39][C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])[C:36]([OH:38])=[O:37])=[O:33])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1>ClCCl>[CH:26]1[C:27]2[CH:28]([CH2:30][O:31][C:32]([NH:34][C@@H:35]([CH2:39][C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])[C:36]([O:38][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([CH3:7])[CH3:6])=[O:37])=[O:33])[C:29]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]=2[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 10715692Fmoc-Asp(OAll)-OH2×HCID 111405172-Phenylpropan-2-yl 2,2,2-trichloroacetimidate

Product 1

HCID 10529786HCID 10529786, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenylpropan-2-yl 2,2,2-trichloroacetimidate separately synthesized by a conventional method (2.17 g, 7.74 mmol) was added to a solution of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid (Compound 106) (1.80 g, 4.55 mmol) in dichloromethane (40 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→65/35) to afford 4-allyl 1-(2-phenylpropan-2-yl) (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)succinate (Compound 107) (2.17 g, 93%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→65/35)

Sources & evidence

ORD record
ord-6e093786928743a3b2a6901df136399a
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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