Hydrochloric Acid → HCID 178451946, compound

HRID 1982303Notes

Reaction equation

HRID 1982303 reaction equation
[N:1]1([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:47][CH2:46][CH2:45][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:44][CH2:43][CH2:42][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([O:40]C)=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4].[OH-].[Na+].Cl.C(O)CCC.O>CO.O>[N:1]1([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:47][CH2:46][CH2:45][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:44][CH2:43][CH2:42][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([OH:40])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22253497Water butanolHCID 178501413HCID 178501413, compound

Product 1

HCID 178451946HCID 178451946, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

17.2 g of crude Boc-Pro-His-Pro-Phe-His-OMe are dissolved in 54 ml of MeOH, 650 ml of 0.1N NaOH are added, the whole is left to stand for 15 minutes at 25°, neutralised by the addition of 650 ml of 0.1N HCl concentratod to dryness. The residue is dissolved in 120 ml of H2O, the pH value is adjusted exactly to 6.8 and this solution is subjected in the system n-butanol/H2O to Craig partitioning over 500 stages; (K=2.8). The fractions that are pure according to thin layer chromagotraphy analysis are combined, concentrated to dryness, dissolved in H2O and lyophilised, yielding Boc-Pro-His-Pro-Phe-His-OH in amorphous form; Rf (A)=0,15; Rf (C)=0.42; Rf (E)=0.25.

Workup

  1. waitthe whole is left
  2. custompartitioning over 500 stages
  3. concentrationconcentrated to dryness
  4. dissolutiondissolved in H2O

Sources & evidence

ORD record
ord-df5f36157d0d451b8bb091ed24559c0b
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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