Sodium Hydroxide → HCID 1587547, compound

HRID 355332Notes

Reaction equation

HRID 355332 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][C:14]([O-:16])=[O:15])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1>[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1587546HCID 1587546, compound

Product 1

HCID 1587547HCID 1587547, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate (1.60 g, 5.11 mmol), 1 M NaOH (25 mL) and THF (25 mL) is stirred 18 hours at ambient temperature. The reaction is concentrated in vacuo to remove THF, the residue diluted with 30 mL H2O, and washed with (3×25 mL) Et2O. The aqueous phase is brought to pH=3 with concentration. HCl and the resulting precipitate collected and dried to afford 1.40 g (4.69 mmol, 92%) product as a white solid. mp 135° C.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. customto remove THF
  3. additionthe residue diluted with 30 mL H2O
  4. washwashed with (3×25 mL) Et2O
  5. concentrationThe aqueous phase is brought to pH=3 with concentration
  6. customHCl and the resulting precipitate collected
  7. customdried

Sources & evidence

ORD record
ord-af9de0c44d9d47d7b9b5ac8025a49865
Source dataset
uspto-grants-1998_11
Patent number
US05830869

Reaction notes

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