Phenyl chloroformate → HCID 131719305, compound

HRID 977523Notes

Reaction equation

HRID 977523 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@@H:10]([C:25]([NH:27][C@@H:28]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:30][CH2:31][CH3:32])=[O:26])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]([O:23][CH3:24])=[O:22])[CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl[C:41]([O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:42]>N1C=CC=CC=1>[C:44]1([O:43][C:41]([NH:1][C@H:2]([C:7]([NH:9][C@@H:10]([C:25]([NH:27][C@@H:28]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:30][CH2:31][CH3:32])=[O:26])[CH2:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([O:23][CH3:24])=[O:22])[CH:13]=2)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:42])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 131719306HCID 131719306, compound

Product 1

HCID 131719305HCID 131719305, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of H-Leu-DTrp(COOMe)-DNle-OtBu (320 mg, prepared in Example 21-(2)) in pyridine (2.3 ml) was added phenyl chloroformate at 0°-5° C. under argon atmosphere. The mixture was stirred at the same temperature for 1.5 h and concentrated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with 10% aq. citric acid, sat. aq. NaHCO3 and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel flash chromatography (Merck, Kieselgel 60) with ethyl acetate/hexane=2/1 for elution to give the product (337 mg).

Workup

  1. customat 0°-5° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with 10% aq. citric acid, sat. aq. NaHCO3 and brine successively
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (Merck, Kieselgel 60) with ethyl acetate/hexane=2/1 for elution

Sources & evidence

ORD record
ord-f9020fbffb7d43f0b2909ae9ef7701b7
Source dataset
uspto-grants-1997_03
Patent number
US05614498

Reaction notes

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