Carbon Dioxide → H-Sta-Val-Tyr-Lys(Boc)-OMe

HRID 1982301Notes

Reaction equation

HRID 1982301 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:29]([NH:31][C@H:32]([C:45]([O:47][CH3:48])=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(=O)=O>CO>[NH2:1][C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:29]([NH:31][C@H:32]([C:45]([O:47][CH3:48])=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:18])[CH:14]([CH3:15])[CH3:16])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 131714720Z-Sta-Val-Tyr-Lys(Boc)-OMe

Product 1

HCID 131714719H-Sta-Val-Tyr-Lys(Boc)-OMe

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

850 mg of Z-Sta-Val-Tyr-Lys(Boc)-OMe are dissolved in 17 ml of 95% strength MeOH and hydrogenated with 85 mg of Pd-on-carbon with CO2 -absorption until saturation (approximately 1 hour). The catalyst is filtered off, the filtrate is concentrated to dryness and dried in a high vacuum at 40° yielding H-Sta-Val-Tyr-Lys(Boc)-OMe in the form of an amorphous powder; Rf (E)=0.58; Rf (H)=0.50. The resulting product is further reacted in stage 1.10.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. customdried in a high vacuum at 40°

Sources & evidence

ORD record
ord-57c5490ac4d4462e8d97d7c2240651ba
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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