Water → HCID 178454126, compound

HRID 707268Notes

Reaction equation

HRID 707268 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.[N+](C1C=CC(C([O:17][C@H:18]2[CH2:21][C@H:20]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]2)=O)=CC=1)([O-])=O>CO>[C:26]([O:25][C:23](=[O:24])[NH:22][C@H:20]1[CH2:21][C@H:18]([OH:17])[CH2:19]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178454134HCID 178454134, compound

Product 1

HCID 178454126HCID 178454126, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of potassium carbonate (5.24 mL, 87 mmol) and water (100 mL) and MeOH (400 mL), was added trans-3-((tert-butoxycarbonyl)amino)cyclobutyl 4-nitrobenzoate (17.1 g, 50.8 mmol). The resulting mixture was heated to 100° C. for 2 h, cooled, and filtered. The filtrate was evaporated under vacuum to give the desired product tert-butyl(trans-3-hydroxycyclobutyl)carbamate (4.4 g, 23.50 mmol, 46.2% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.73 (br. s., 1 H), 4.39-4.58 (m, 1 H), 4.22 (br. s., 1 H), 2.10-2.48 (m, 5 H), 1.44 (s, 9 H).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-50b7aab533fe45e688ac4fab61581abd
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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