HCID 59201629, compound → HCID 59201321, compound

HRID 451871Notes

Reaction equation

HRID 451871 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH3:21])([CH3:20])[CH2:5][C@H:6]1[CH2:10][O:9]C(C)(C)[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CC(O)=O>[OH:9][CH2:10][C@@H:6]([NH:7][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:5][C:4]([CH3:21])([CH3:20])[CH2:3][O:2][CH3:1]

Participants

3

Reactant 1

HCID 59201629HCID 59201629, compound

Product 1

HCID 59201321HCID 59201321, compoundYield 140.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

(S)-tert-butyl 4-(3-methoxy-2,2-dimethylpropyl)-2,2-dimethyloxazolidine-3-carboxylate (6.4 g, 21.3 mmol) was dissolved in 70% CH3COOH. The solution was heated to 50-60° C. and stirred for 2 h. The reaction solution was evaporated to give (S)-tert-butyl 1-hydroxy-5-methoxy-4,4-dimethylpentan-2-ylcarbamate (7.8 g, 100%) as an oil that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ3.69 (m, 3H), 3.32 (s, 3H), 3.01 (m, 2H), 2.11 (s, 7H), 1.48 (m, 10H), 1.23 (m, 22H), 0.91 (m, 18H).

Workup

  1. customThe reaction solution was evaporated

Sources & evidence

ORD record
ord-e4bae5cf4b0341258fbde4715beb430e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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