HCID 22942128, compound → HCID 86753708, compound

HRID 362123Notes

Reaction equation

HRID 362123 reaction equation
[CH2:1]([O:8][C:9](=[O:78])[C@H:10]([CH2:74][CH:75]([CH3:77])[CH3:76])[NH:11][C:12](=[O:73])[C@H:13]([C:69]([CH3:72])([CH3:71])[CH3:70])[NH:14][C:15](=[O:68])[C@H:16]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=1[CH3:67])[NH:17][C:18](=[O:59])[C@H:19]([CH2:50][CH2:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[NH:20][C:21](=[O:49])[C@H:22]([CH2:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[NH:23]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:78])[C@H:10]([CH2:74][CH:75]([CH3:76])[CH3:77])[NH:11][C:12](=[O:73])[C@H:13]([C:69]([CH3:72])([CH3:71])[CH3:70])[NH:14][C:15](=[O:68])[C@H:16]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=1[CH3:67])[NH:17][C:18](=[O:59])[C@H:19]([CH2:50][CH2:51][C:52](=[O:58])[O:53][C:54]([CH3:55])([CH3:56])[CH3:57])[NH:20][C:21](=[O:49])[C@H:22]([CH2:41][C:42](=[O:48])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[NH2:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22942128HCID 22942128, compound

Product 1

HCID 86753708HCID 86753708, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

A solution of 10.088 g (9.4 mmol) of N-[N-[N-[N-[N-[(9-fluorenyl)methoxycarbonyl] O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-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-[N-[O-tert-butyl-L-α-aspartyl]-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-2fbc72ecd0f74ca5b9e12b3a92152827
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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