tert-Butanol → Methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-3-(4-chlorophenyl)propanoate

HRID 79500Notes

Reaction equation

HRID 79500 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([CH2:23][CH:24]([C:29]([O:31][CH3:32])=[O:30])[CH2:25]C(O)=O)=[CH:21][CH:20]=1.C([N:37]([CH2:40]C)CC)C.[CH3:42][C:43]([OH:46])([CH3:45])[CH3:44]>>[C:43]([O:46][C:40]([NH:37][CH2:25][CH:24]([CH2:23][C:22]1[CH:21]=[CH:20][C:19]([Cl:18])=[CH:34][CH:33]=1)[C:29]([O:31][CH3:32])=[O:30])=[O:8])([CH3:45])([CH3:44])[CH3:42]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 142705963-(4-Chlorobenzyl)-4-methoxy-4-oxobutanoic acid

Product 1

HCID 44890986Methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-3-(4-chlorophenyl)propanoateYield 31%

Procedure

Diphenylphosphoryl azide (2.1 g, 76 mmol) was added to a solution of 3-(4-chlorobenzyl)-4-methoxy-4-oxobutanoic acid (1.6 g, 6.4 mmol) and triethylamine (“TEA”; 0.97 g, 9.58 mmol) in t-BuOH (40 mL). The reaction mixture was then heated to reflux and stirred for 6 hours. The reaction was then cooled to room temperature and concentrated to an oil. Purification by column chromatography (9:1 to 5:1 hexane:EtOAc) gave methyl 3-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)propanoate (0.64 g, 31%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. concentrationconcentrated to an oil
  4. customPurification by column chromatography (9:1 to 5:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-37ab3cda0b774a048a6f941dc6ce6ee8
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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