Acetonitrile → Methyl N1-[2-[(4-chlorophenyl)carbonyl]-4-(methyloxy)phenyl]-N2-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-alpha-asparaginate

HRID 2201331Notes

Reaction equation

HRID 2201331 reaction equation
C[N:2]([C:11]([O:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[C@H:3]([C:8](Cl)=[O:9])[CH2:4][C:5](=[O:7])[OH:6].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=1[C:37]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)=[O:38].[C:46](#N)C>C(Cl)(Cl)Cl>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([C:37]([C:30]2[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:29]=2[NH:28][C:8](=[O:9])[C@H:3]([CH2:4][C:5]([O:6][CH3:46])=[O:7])[NH:2][C:11]([O:13][CH2:14][CH:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:22]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:12])=[O:38])=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 13408099(2-Amino-5-methoxyphenyl)(4-chlorophenyl)methanoneHCID 86668915Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl]-L-alpha-aspartyl chloride

Product 1

HCID 67173295Methyl N1-[2-[(4-chlorophenyl)carbonyl]-4-(methyloxy)phenyl]-N2-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-alpha-asparaginate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-α-aspartyl chloride (Int. J. Peptide Protein Res. 1992, 40, 13-18) (93 g, 0.24 mol) was dissolved in CHCl3 (270 mL) and [2-amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone (53 g, 0.2 mol) (for a preparation see Reference compound B) was added. The resulting mixture was stirred at 60° C. for 1 h before being cooled and concentrated at 60% in volume. Ether was added at 0° C. and the resulting precipitate was filtered and discarded. The filtrate was concentrated under reduced pressure and used without further purification.

Workup

  1. additionwas added
  2. temperaturebefore being cooled
  3. concentrationconcentrated at 60% in volume
  4. additionEther was added at 0° C.
  5. filtrationthe resulting precipitate was filtered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customused without further purification

Sources & evidence

ORD record
ord-465307f84b704131a9c5bf037ab7e736
Source dataset
uspto-grants-2016_06
Patent number
US09360482B2

Reaction notes

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