Acetic Anhydride → HCID 69928763, compound

HRID 536995Notes

Reaction equation

HRID 536995 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH:13]([OH:17])[C:14]([OH:16])=[O:15])[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:17][CH:13]([C:9]1([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12][CH2:11][CH2:10]1)[C:14]([OH:16])=[O:15])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67230310HCID 67230310, compound

Product 1

HCID 69928763HCID 69928763, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(1-Tert-butoxycarbonylaminocyclobutyl)-hydroxyacetic acid (201.5 mg, 0.822 mmol) was stirred with acetic anhydride (95 mL) in pyridine (1.5 mL) for 24 h. The mixture was first concentrated under vacuum, and then diluted with 5 mL EtOAc. The organic solution was washed with 1N HCl (2 mL) followed by saturated aqueous NaCl (2 mL), dried (Na2SO4), and evaporated under vacuum which gave the title compound. LC-UV/MS API-ES− m/z 286 [M−H]−1H NMR (400 MHz, DMSO-d6) δ ppm 7.11 (s, 1H), 5.00 (s, 1H, CHOAc), 2.28 (m, 2H), 2.07 (s, 3H, Me), 2.04 (m, 2H), 1.81 (m, 1H), 1.67 (m, 1H), 1.35 (s, 9H, Boc).

Workup

  1. concentrationThe mixture was first concentrated under vacuum
  2. additiondiluted with 5 mL EtOAc
  3. washThe organic solution was washed with 1N HCl (2 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum which

Sources & evidence

ORD record
ord-d04aaecea0794decb8846359ac376e40
Source dataset
uspto-grants-2014_10
Patent number
US08859605B2

Reaction notes

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