Sodium Hydroxide → HCID 22458740, compound

HRID 2185438Notes

Reaction equation

HRID 2185438 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:26])[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12][CH:11]1[C:27]([O:29]C)=[O:28])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:26])[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:12][CH:11]1[C:27]([OH:29])=[O:28])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70175459HCID 70175459, compound

Product 1

HCID 22458740HCID 22458740, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 N sodium hydroxide (728 mL) was added to a stirred solution of Methyl 1-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylglycyl)piperazine-2-carboxylate (A, 195 mg) in methanol (3 mL). The mixture was stirred at room temperature for 23 hr and evaporated in vacuo. The residue was diluted with water and washed with ether. The aqueous layer was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (186 mg) as a colorless solid: 1H NMR (400 MHz, CD3OD) δ 1.44 (br s, 18H) and 2.70-4.80 (m, 9H).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with water
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c2b69ebc3d414a5788248a0f954144d7
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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