Ethyl Acetate → tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)-3-(4-bromophenyl)propan-2-yl)carbamate

HRID 1429364Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:36])C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(=O)OCC>C1COCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][Br:36])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 3h (4.15 g, 9.2 mmol) in dry THF (50 mL) was added NBS (4.1 g, 23 mmol) and PPh3 (6 g, 23 mmol) at 0° C. The mixture was stirred at 0° C. for 20 min. Then the mixture was stirred at rt for 2 hr. The solvent was evaporated in vacuo and purified by CC eluting with PE:EA=4:1 to give 3i as a white solid (2.3 g, 50% yield).

Workup

stirringThen the mixture was stirred at rt for 2 hr
customThe solvent was evaporated in vacuo
custompurified by CC
washeluting with PE

Sources & evidence

ORD record: ord-67bd00b7885d4893a4db9754282a1d4d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940722B2

Reaction notes

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