Hydrochloric Acid → Boc-Thr(Bzl)-Pro-OH

HRID 435394Notes

Reaction equation

HRID 435394 reaction equation
[NH:1]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:2]([C:13]([N:15]1[CH2:29][CH2:28][CH2:27][C@H:16]1[C:17]([O:19]CC1C=CC=CC=1)=[O:18])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[NH:1]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[C@H:2]([C:13]([N:15]1[CH2:29][CH2:28][CH2:27][C@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15003996BOC-Thr(Bzl)-Pro-OBzl

Product 1

HCID 13091018Boc-Thr(Bzl)-Pro-OHYield 77.75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Substance [5] (52.78 g, 106.29 mM) was dissolved in methanol (300 ml). 1 N NaOH (150 ml, 1.4 molar excess) was added dropwise during 20 minutes with ice cooling and then the mixture was stirred at room temperature. 1 N HCl (43.71 ml, 0.4 molar excess) was added with ice cooling to adjust to pH 7 and methanol was distilled off in vacuo. The aqueous layer was washed with ether (150 ml) and the pH of the aqueous layer was adjusted to pH 3 by adding 1 N HCl (110 ml). The solution was extracted twice with ethyl acetate (300 ml and 150 ml). The extract was dried by adding anhydrous sodium sulfate, then concentrated in vacuo. Ether and hexane were added to the residue to obtain the precipitate. The same operation was repeated and the precipitate was dissolved in ethyl acetate, then dried in vacuo to obtain the foaming solid substance [6] (32.27 g, yield: 77.75%).

Workup

  1. distillationwas distilled off in vacuo
  2. washThe aqueous layer was washed with ether (150 ml)
  3. additionby adding 1 N HCl (110 ml)
  4. extractionThe solution was extracted twice with ethyl acetate (300 ml and 150 ml)
  5. customThe extract was dried
  6. additionby adding anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. additionEther and hexane were added to the residue
  9. customto obtain the precipitate
  10. customdried in vacuo

Sources & evidence

ORD record
ord-c580b07cec9a4d319c2cc1dba9750e7b
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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