Ethanol → Z-Phe-His-Leu-Val 7-(pivaloyloxymethoxycarbonyl)-heptyl amide

HRID 65354Notes

Reaction equation

HRID 65354 reaction equation
[NH:1]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C@H:2]([C:10]([NH:12][C@H:13]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@H:31]([C:35]([OH:37])=[O:36])[CH:32]([CH3:34])[CH3:33])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:48]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH-:58])([OH:50])=[O:49].[OH-:59].[Na+].[CH2:61](O)C>>[NH:1]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C@H:2]([C:10]([NH:12][C@H:13]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@H:31]([C:35]([OH:37])=[O:36])[CH:32]([CH3:34])[CH3:33])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[C:41]([O:40][CH2:38][O:49][C:48]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH-:58])=[O:50])(=[O:59])[C:42]([CH3:47])([CH3:61])[CH3:43]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 178445988HCID 178445988, compound

Product 1

HCID 178447589Z-Phe-His-Leu-Val 7-(pivaloyloxymethoxycarbonyl)-heptyl amide

Procedure

40 mg of Z-Phe-His-Leu-Val-7-carboxyheptyl amide (Example 29) are made into a slurry in 1 ml of ethanol and 100 μl of 1N NaOH are added. The solution is concentrated by evaporation and dried by twice making into a slurry in toluene/ethanol and concentrating by evaporation. The residue is dissolved in 0.5 ml of DMF; at 0° while stirring 12 mg of pivalic acid iodomethyl ester in 0.2 ml of DMF are added twice at an interval of 1 hour, the whole is further stirred for 16 hours at 0° and for 1 hour at room temperature and then evaporated to dryness in a high vacuum. The title compound is obtained by flash chromatography (5.5 g of silica gel, eluant methylene chloride/methanol/conecentrated ammonia 700:50:1) of the residue. Rf (B11)=0.81 Rf (methylene chloride/methanol/concentrated ammonia 700:50:1)=0.23.

Workup

  1. concentrationThe solution is concentrated by evaporation
  2. customdried
  3. concentrationconcentrating by evaporation
  4. dissolutionThe residue is dissolved in 0.5 ml of DMF
  5. additionare added twice at an interval of 1 hour
  6. stirringthe whole is further stirred for 16 hours at 0° and for 1 hour at room temperature
  7. customevaporated to dryness in a high vacuum

Sources & evidence

ORD record
ord-39cff86c58cd4d7f94977af85e595c90
Source dataset
uspto-grants-1986_09
Patent number
US04613676

Reaction notes

Loading…