Hydrochloric Acid → Boc-ala-pro-OH

HRID 435402Notes

Reaction equation

HRID 435402 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:3].[OH-].[Na+].Cl>C(O)C>[NH:1]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 13068139N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-L-proline phenylmethyl ester

Product 1

HCID 11902919Boc-ala-pro-OHYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The substance [24] was dissolved in ethanol (200 ml). 1 N NaOH (240 ml, 1.2 molar excess) was added dropwise at 0° C. and the mixture was stirred at room temperature. After two hours, 1 N NaOH (20 ml) was added and the mixture was further stirred for 30 minutes. The reaction mixture was neutralized with 1 N HCl (60 ml) at 0° C., and the ethanol was distilled off in vacuo. After twice washing the aqueous layer with ether (100 ml), 1 N HCl (200 ml) was added thereto at 0° C. The precipitate thus formed was filtered, washed completely and dried in vacuo. Recrystallization was effected from ethyl acetate (450 ml)-hexane to crystallize the substance [25] (47.92 g, yield: 83.8%).

Workup

  1. stirringthe mixture was further stirred for 30 minutes
  2. distillationthe ethanol was distilled off in vacuo
  3. washAfter twice washing the aqueous layer with ether (100 ml), 1 N HCl (200 ml)
  4. additionwas added
  5. customat 0° C
  6. customThe precipitate thus formed
  7. filtrationwas filtered
  8. washwashed completely
  9. customdried in vacuo
  10. customRecrystallization

Sources & evidence

ORD record
ord-6ecc681bcbc94645b61bf154cafc569f
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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