Benzyl Alcohol → HCID 68856262, compound

HRID 28439Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[CH2:7][CH:8]([CH2:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][CH3:16])C(O)=O)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])=CC=1.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CC[N:47]([CH2:50]C)CC>>[C:1]([O:5][C:6](=[O:19])[CH2:7][C@@H:8]([NH:47][C:50]([O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:27])[CH2:12][C:13]([CH3:17])([CH3:18])[CH2:14][CH2:15][CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 4

HCID 244Benzyl Alcohol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 876026502-(2,2-Dimethyl-pentyl)-succinic acid 4-tert-butyl ester

Product 1

HCID 68856262HCID 68856262, compound

Procedure

According to example 1, 2.14 g (7.9 mmol)of 2-(2,2-dimethyl-pentyl)-succinic acid 4-tert-butyl ester, 1.7 mL of DPPA, 1.1 mL of Et3N and 2.44 mL of BnOH provided 1.63 g (54.8% in two steps) of the title compound as an oil. 1HNMR (400 MHz; CDCl3): 0.78-0.89 (m, 9H), 1.10-1.30 (m, 5H), 1.36 (s, 9H), 2.39 (t, 2H, J=5 Hz), 4.95-4.05 (m, 1H), 5.00 (s, 2H), 5.09 (d, 1H, J=9.6 Hz), 7.22-7.30 (m, 5H).

Sources & evidence

ORD record: ord-7e92382628dc4663a76f77b87ab42718
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419981B2

Reaction notes

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