Piperidine → HCID 178511795, compound

HRID 355527Notes

Reaction equation

HRID 355527 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H:2]([C:9]([NH:11][C@H:12]([C:28]([NH:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.N1CCCCC1>ClCl>[NH2:1][C@@H:2]([C:9]([NH:11][C@H:12]([C:28]([NH:30][CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:16][CH:15]=1)=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 178523873HCID 178523873, compound

Product 1

HCID 178511795HCID 178511795, compound

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

Fmoc-D-His-Tyr(OBn)-CONH(CH2)2Ph (0.6 g, 0.8 mmol) in CH2 Cl2 (5 mL) was treated with piperdine (0.14 g, 1.6 mmol). The resulting mixture was stirred 2 hours before concentrating in vacuo and purifying the resulting by flash chromatography (SiO2, CHCl3 :MeOH eluent) to give D-His-Tyr(OBn)-CONH(CH2)2Ph. The foam was dissolved in CH2C2 (5 mL) and treated with 4-phenoxyphenyl isocyanate (0.05 g, 0.23 mmol). The resulting mixture was stirred 1 hour at room temperature, concentrated in vacuo, and purified the resulting oil by flash chromatography (SiO2, CHCl3 :MeOH eluent) to obtain (4-PhOPh)NHCO-D-His-Tyr(OBn)-CONH(CH2)2Ph as a foam; ES-MS 723 (m+1).

Workup

  1. concentrationbefore concentrating in vacuo
  2. custompurifying the resulting by flash chromatography (SiO2, CHCl3 :MeOH eluent)

Sources & evidence

ORD record
ord-29608e34a24f4ef1bb305245c5035a26
Source dataset
uspto-grants-1998_11
Patent number
US05830868

Reaction notes

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