Sodium Hydroxide → HCID 6917550, compound

HRID 620217Notes

Reaction equation

HRID 620217 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]([CH3:44])([O:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:26](NC(CC1CCCCC1)C(=O)C(=O)CCC)=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH3:5]>CO>[C:4]([O:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:26]([OH:1])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])([CH3:44])([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70089787HCID 70089787, compound

Product 1

HCID 6917550HCID 6917550, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (1N; 12 ml, 12 mmol) was added to a 40 ml methanol solution of (S)-<α-[[(1,1-dimethylethoxy)carbonyl]amino]cyclohexanepropanoic acid, methyl ester (3.92 g, 10 mmol) and a chromatography check after one hour revealed total disappearance of starting material. The solvents were removed on rotary evaporator. The resulting white solid was suspended in 10 ml of water and 50 ml of ethyl acetate, acidified to pH=3.5 using 1N hydrochloric acid and the two layers separated. The aqueous layer was reextracted with ethyl acetate (3×30 ml), combined organic extracts dried over sodium sulfate and concentrated to give 3.54 g of the title E compound.

Workup

  1. customThe solvents were removed on rotary evaporator
  2. customthe two layers separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give 3.54 g of the title E compound

Sources & evidence

ORD record
ord-bd6fefe5fc6047ae9dd512be50ce81e3
Source dataset
uspto-grants-1989_04
Patent number
US04820691

Reaction notes

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