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

HRID 882309Notes

Reaction equation

HRID 882309 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].[CH:46](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

4

Reactant 3

HCID 6212ChloroformHCID 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

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 (for a preparation see Reference compound B) (53 g, 0.2 mol) was added. The resulting mixture was stirred at 60° C. for 1 h before being cooled and concentrated to 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 to 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-9f21c03cf0b74c039b5169d1caf07b1a
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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