Hydrochloric Acid → HCID 178465149, compound

HRID 1395822Notes

Reaction equation

HRID 1395822 reaction equation
C[O:2][C:3](=[O:77])[C:4](=[CH2:76])[NH:5][C:6](=[O:75])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:74])[C@H:13]([CH2:68][C:69]1[N:73]=[CH:72][NH:71][CH:70]=1)[NH:14][C:15](=[O:67])[C@H:16]([C@H:63]([CH2:65][CH3:66])[CH3:64])[NH:17][C:18](=[O:62])[C@H:19]([CH2:54][C:55]1[CH:60]=[CH:59][C:58]([OH:61])=[CH:57][CH:56]=1)[NH:20][C:21](=[O:53])[C@H:22]([CH:50]([CH3:52])[CH3:51])[NH:23][C:24](=[O:49])[C@H:25]([CH2:42][CH2:43][CH2:44][NH:45][C:46](=[NH:48])[NH2:47])[N:26]([C:30](=[O:41])[CH2:31][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH3:33])[N+:27]([O-:29])=[O:28].[OH-].[Li+].Cl>O1CCOCC1>[C:37]([O:36][C:34]([N:32]([CH2:31][C:30]([N:26]([N+:27]([O-:29])=[O:28])[C@H:25]([C:24]([NH:23][C@H:22]([C:21]([NH:20][C@H:19]([C:18]([NH:17][C@H:16]([C:15]([NH:14][C@H:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([NH:5][C:4]([C:3]([OH:77])=[O:2])=[CH2:76])=[O:75])=[O:74])[CH2:68][C:69]1[N:73]=[CH:72][NH:71][CH:70]=1)=[O:67])[C@H:63]([CH2:65][CH3:66])[CH3:64])=[O:62])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([OH:61])=[CH:57][CH:56]=1)=[O:53])[CH:50]([CH3:51])[CH3:52])=[O:49])[CH2:42][CH2:43][CH2:44][NH:45][C:46](=[NH:47])[NH2:48])=[O:41])[CH3:33])=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178465150HCID 178465150, compound

Product 1

HCID 178465149HCID 178465149, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.09 g of t-butoxycarbonylsarcosylnitroarginylvalyltyrosylisoleucylhistidylprolyldehydroalanine methyl ester is dissolved in 30 ml of dioxane. To this solution is added 60 ml of 1 N lithium hydroxide. The reaction mixture is stirred for three hours, then neutralized with 1 N hydrochloric acid to pH 7. The solvent is removed by vacuum and the residue is dissolved in N,N-dimethylformamide. Ths solution is filtered and the solvent removed by vacuum. The residue is dissolved in dioxane and added to 300 ml of cold rapidly stirring ethyl ether. The precipate is filtered and dried in vacuo to afford t-butoxycarbonylsarcosylnitroarginylvalyltyrosylisoleucylhistidylprolyldehydroalanine.

Workup

  1. customThe solvent is removed by vacuum
  2. dissolutionthe residue is dissolved in N,N-dimethylformamide
  3. filtrationThs solution is filtered
  4. customthe solvent removed by vacuum
  5. dissolutionThe residue is dissolved in dioxane
  6. additionadded to 300 ml of cold rapidly stirring ethyl ether
  7. filtrationThe precipate is filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e8940fc6362646668d5fb0de49810923
Source dataset
uspto-grants-1980_05
Patent number
US04204991

Reaction notes

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