Dimethylformamide → HCID 59894806, compound

HRID 2184654Notes

Reaction equation

HRID 2184654 reaction equation
CN(C=O)C.[NH:6]1[C:39](=[O:40])[C@H:38]2[CH2:41][CH2:42][CH2:43][N:37]2[C:35](=[O:36])[C@H:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH:26][C:24](=[O:25])[C@H:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:15][C:13](=[O:14])[C@@H:7]1[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12].Cl.[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(O)(=O)C>[NH:6]1[C:39](=[O:40])[C@H:38]2[CH2:41][CH2:42][CH2:43][N:37]2[C:35](=[O:36])[C@H:27]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:26][C:24](=[O:25])[C@H:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:15][C:13](=[O:14])[C@@H:7]1[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:45]([CH3:46])=[O:47]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 131723244HCID 131723244, compound

Product 1

HCID 59894806HCID 59894806, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a DMF (2 ml) solution of the cyclo(-L-Lys-L-Phe-L-Phe-D-Pro-).HCl (44 mg, 80 mmol) obtained in step 10-1, TEA(33 ml, 0.24 mmol) and acetic anhydride (12 ml, 0.12 mmol) were added under ice cooling and stirred for 2 hours. The reaction mixture was neutralized by addition of acetic acid and concentrated. The crude peptide was preparatively purified by reverse-phase HPLC (column: YMC-Pack ODS A-323, 10×250 mm, 30% CH3CH/0.1% TFA) and lyophilized to yield 57 mg (quant) of the titled compound.

Workup

  1. concentrationconcentrated
  2. customThe crude peptide was preparatively purified by reverse-phase HPLC (column: YMC-Pack ODS A-323, 10×250 mm, 30% CH3CH/0.1% TFA)

Sources & evidence

ORD record
ord-f8acbaf44a0e4e02beb1d53069663ce0
Source dataset
uspto-grants-2002_06
Patent number
US06399568B1

Reaction notes

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