Hydrochloric Acid → HCID 178427580, compound

HRID 1632428Notes

Reaction equation

HRID 1632428 reaction equation
[NH:1]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@H:2]([C:20]([NH:22][C@H:23]([C:26]([NH:28][C@H:29]([C:32]([O:34]C)=[O:33])[CH2:30][OH:31])=[O:27])[CH2:24][OH:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[OH-].[Na+].Cl>CO.O>[NH:1]([C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[C@H:2]([C:20]([NH:22][C@H:23]([C:26]([NH:28][C@H:29]([C:32]([OH:34])=[O:33])[CH2:30][OH:31])=[O:27])[CH2:24][OH:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178501488Z-Arg(Tos)-Ser-Ser-OMe

Product 1

HCID 178427580HCID 178427580, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3.5 Grams of Z-Arg(Tos)-Ser-Ser-OMe was dissolved in 50 ml of methanol and 10 ml of water, and 8.06 ml of 1N-sodium hydroxide was added thereto, the mixture was stirred at a room temperature for 45 minutes, next 7.24 ml of 1N-HCl was added to neutralize the reaction mixture, then methanol was removed by distillation, and the residue was extracted with n-butanol. The extract was washed with water, and n-butanol and water were removed by distillation, the residue was crystallized by adding ether, reprecipitated from methanol-ethyl acetate to obtain 2.60 g of Z-Arg(Tos)-Ser-Ser-OH.

Workup

  1. custommethanol was removed by distillation
  2. extractionthe residue was extracted with n-butanol
  3. washThe extract was washed with water, and n-butanol and water
  4. customwere removed by distillation
  5. customthe residue was crystallized
  6. additionby adding ether
  7. customreprecipitated from methanol-ethyl acetate

Sources & evidence

ORD record
ord-88e1ea7a4dd344b3aa948d17bb5e1482
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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