2,2,2-Trichloro-tert-butyl chloroformate → (rac.)-(1R,5S)-7-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic Acid 3-tert-butyl Ester 6-ethyl Ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) Ester

HRID 2428173Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[CH:12][C@H:11]2[N:28](C)[C@@H:7]1[CH2:8][N:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10]2)=[O:5])[CH3:2].Cl[C:38]([O:40][C:41]([CH3:47])([CH3:46])[C:42]([Cl:45])([Cl:44])[Cl:43])=[O:39]>ClCCCl>[Cl:43][C:42]([Cl:45])([Cl:44])[C:41]([O:40][C:38]([N:28]1[C@H:7]2[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][Si:21]([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:22])[CH3:23])=[CH:18][CH:19]=3)[CH2:12][C@@H:11]1[CH2:10][N:9]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:8]2)=[O:39])([CH3:47])[CH3:46]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of compound B9 (6.16 g, 11.9 mmol) and 2,2,2-trichloro-1,1-dimethylethyl chloroformate (3.15 g, 13.1 mmol) in 1,2-dichloroethane (200 mL) was heated to 60° C. for 20 h. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 8:2) yielded the title compound (7.58 g, 90%). LC-MS: tR=1.29 min, ES+: 707.36.

Workup

temperatureto cool to rt
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (EtOAc/heptane 8:2)

Sources & evidence

ORD record: ord-d3aef1d984244af2a5b47a8586fecde5
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968720B2

Reaction notes

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