Acetyl chloride → 4-Acetylamino-4-(2-tert-butoxycarbonyl-ethyl)-heptanedioic acid di-tert-butyl ester

HRID 2280241Notes

Reaction equation

[NH2:1][C:2]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][C:2]([NH:1][C:37](=[O:39])[CH3:38])([CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To 5 ml CH2Cl2 was added 1 g of triester 62 (2.4 mmol, 1 equiv) and 0.3 g triethylamine (2.9 mmol, 1.2 equiv.) The solution was cooled to 0° C. with an ice bath and 0.23 g acetyl chloride (2.9 mmol, 1.2 equiv) was added dropwise. The solution was stirred for a further 4 hours and allowed to warm slowly to room temperature. The solution was poured into a separating funnel and washed with 2×15 ml HCl (5% aqueous) and 1×15 ml concentrated NaCl. The solution was dried over Na2SO4 and the solvent was removed in vacuo. The residue was dissolved in minimal EtOAc and loaded onto a silica column, where it was purified by column chromatography with EtOAc and hexane (1:1) to give 0.79 g of a white solid in 72% yield.

Workup

temperatureto warm slowly to room temperature
additionThe solution was poured into a separating funnel
washwashed with 2×15 ml HCl (5% aqueous) and 1×15 ml concentrated NaCl
dry with materialThe solution was dried over Na2SO4
customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in minimal EtOAc
customwas purified by column chromatography with EtOAc and hexane (1:1)

Sources & evidence

ORD record: ord-65ab3c6af2a04f2e9ee8be0e5f6ae8a0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09138495B2

Reaction notes

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