Acetic Acid → N-Cbz-d-alanine

HRID 1714582Notes

Reaction equation

HRID 1714582 reaction equation
C([O-])(=O)C.[Na+].C(O)(=O)C.IC1C=CC(C2N=[C:19]([C@H:23]([N:25](C)[C:26](=[O:35])[O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)C)N(C)C=2)=CC=1.[C:37]([O-:40])([OH:39])=O.[Na+]>O1CCOCC1>[NH:25]([C:26]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:35])[C@@H:23]([C:37]([OH:40])=[O:39])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 57594310HCID 57594310, compound2×

Product 1

HCID 70832N-Cbz-d-alanineYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-amino-4′-bromoacetophene hydrochloride (10.0 g, 40 mmol), sodium acetate (16.4 g, 200 mmol), acetic acid (11.5 mL, 200 mmol) and compound 2 (19.2 g, 80 mmol) in dioxane (70 mL) was stirred at 65° C. until TLC showed no compound 2 left (about 2 h). The reaction mixture was carefully neutralized with saturated NaHCO3 solution and extracted with ethyl acetate. The organic solution was dried over Na2SO4 and concentrated. Purification with flash column chromatography (EtOAc:Hexs 1:1) gave product 3 (9.11 g, 79%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification with flash column chromatography (EtOAc:Hexs 1:1)

Sources & evidence

ORD record
ord-c898a48e78c8430da5c16afc782b9af7
Source dataset
uspto-grants-2010_09
Patent number
US07795448B2

Reaction notes

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