Benzyl Alcohol → HCID 15042555, compound

HRID 249399Notes

Reaction equation

HRID 249399 reaction equation
[C:1]([C:5]([CH3:11])([CH3:10])[CH2:6]C(O)=O)([O:3][CH3:4])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.C([N:31]([CH2:34]C)CC)C.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1>[CH2:36]([O:43][C:34]([NH:31][CH2:6][C:5]([CH3:11])([CH3:10])[C:1]([O:3][CH3:4])=[O:2])=[O:19])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 150395654-Methoxy-3,3-dimethyl-4-oxobutanoic acid

Product 1

HCID 15042555HCID 15042555, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Carbomethoxy-3-methylbutanoic acid [Bull. Soc. Chim. Fr., 828 (1965), 7.85 g, 0.049 mol] was reacted with diphenylphosphorylazide and triethylamine as described in Example 71. After heating the toluene solution for 1.5 h, benzyl alcohol (8 g) was added directly to the reaction mixture and heating at reflux was continued for 20 h. Work-up and purification as in Example 71 gave methyl 3-benzyloxycarbonylamino-2,2-dimethylpropionate. NMR (300 MHz, CDCl3): 1.2 (s, 6H), 3.3 (d, 2H), 3.68 (s, 3H), 5.1 (s, 2H), 5.22 (m, 1H). A sample of the methyl ester (6.21 g, 0.023 mol) was saponified with 3.1 g (0.78 mol) of NaOH in 100 mL ethanol/10 mL H2O at room temperature for 48 h. Work-up as in Example 71 gave the desired product as a liquid. NMR (300 MHz, CDCl3): 1.23 (s, 6H), 3.32 (d, 2H), 5.10 (s, 2H), 5.27 (m, 1H).

Workup

  1. temperatureheating
  2. temperatureat reflux
  3. custompurification as in Example 71

Sources & evidence

ORD record
ord-111c8a520f254bbebda971d6d22cacbe
Source dataset
uspto-grants-1993_05
Patent number
US05214129

Reaction notes

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