HCID 22942113, compound → HCID 22942135, compound

HRID 635626Notes

Reaction equation

HRID 635626 reaction equation
[CH2:1]([O:8][C:9](=[O:66])[C@H:10]([CH2:62][CH:63]([CH3:65])[CH3:64])[NH:11][C:12](=[O:61])[C@H:13]([C:57]([CH3:60])([CH3:59])[CH3:58])[NH:14][C:15](=[O:56])[C@H:16]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[CH3:55])[NH:17][C:18](=[O:47])[C@H:19]([CH2:38][CH2:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[NH:20]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1CCCCC1.ClCCl>[CH2:1]([O:8][C:9](=[O:66])[C@H:10]([CH2:62][CH:63]([CH3:64])[CH3:65])[NH:11][C:12](=[O:61])[C@H:13]([C:57]([CH3:59])([CH3:58])[CH3:60])[NH:14][C:15](=[O:56])[C@H:16]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[CH3:55])[NH:17][C:18](=[O:47])[C@H:19]([CH2:38][CH2:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[NH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22942113HCID 22942113, compound

Product 1

HCID 22942135HCID 22942135, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

A solution of 10.89 g (12.07 mmol) of N-[N-[N-[N-[(9-fluorenyl)methoxycarbonyl]-O-tert-butyl-L-a-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester in 30 ml of piperidine and 120 ml of dichloromethane was stirred for 30 minutes at room temperature. The solvent was removed by evaporation and the residue was chromatographed on silica gel using firstly 20% ethyl acetate in hexane and then 10% methanol in dichloromethane for the elution. Evaporation gave N-[N-[N-[O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester in the form of an oil which was used in the next step without further purification.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was chromatographed on silica gel using firstly 20% ethyl acetate in hexane
  3. wash10% methanol in dichloromethane for the elution
  4. customEvaporation

Sources & evidence

ORD record
ord-7552071cc90840bcb5864168b62479c6
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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