Sodium Hydroxide → 4-({[(Tert-butoxy)carbonyl]amino}methyl)oxane-4-carboxylic acid

HRID 2047470Notes

Reaction equation

HRID 2047470 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:16]([O:18]CC)=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:16]([OH:18])=[O:17])[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67232523HCID 67232523, compound

Product 1

HCID 170402064-({[(Tert-butoxy)carbonyl]amino}methyl)oxane-4-carboxylic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the compound (11.3 g) obtained in step 3 in methanol (190 mL) was added 2N aqueous sodium hydroxide solution (79 mL), and the mixture was stirred at 40° C. for 2 hr. The mixture was concentrated, diluted with ethyl acetate, and neutralized with 1N hydrochloric acid. The separated aqueous layer was extracted with ethyl acetate. The combined organic layer was dried, and concentrated under reduced pressure to give the title compound (9.3 g, 91%) as a white powder.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. extractionThe separated aqueous layer was extracted with ethyl acetate
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d85702c4879d4744a90d30e575f48e35
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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