Triethylamine → 2-Oxo-2-[4-(trifluoromethoxy)phenyl]ethyl (3-{[(benzyloxy)carbonyl]amino}oxetan-3-yl)acetate

HRID 1523292Notes

Reaction equation

HRID 1523292 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:15][O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)=[O:23].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:16][C:17]([O:19][CH2:21][C:22](=[O:23])[C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=2)=[O:18])[CH2:13][O:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27786912-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-oneHCID 895254372-(3-{[(Benzyloxy)carbonyl]amino}oxetan-3-yl)acetic acid

Product 1

HCID 1231569852-Oxo-2-[4-(trifluoromethoxy)phenyl]ethyl (3-{[(benzyloxy)carbonyl]amino}oxetan-3-yl)acetateYield 107%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(3-{[(Benzyloxy)carbonyl]amino}oxetan-3-yl)acetic acid (Preparation 25, 1.011 Kg, 3.812 mol) was stirred in ethyl acetate (8 L). 2-Bromo-1-[4-(trifluoromethoxy)phenyl]-ethanone (1.08 Kg, 3.81 mol) was added, followed by triethylamine (585 mL, 4.19 mol). The reaction was initially fully solubilised, but a precipitate was then observed. The reaction was washed with water (2×4 L), then concentrated in vacuo to afford the title compound as a mobile orange oil (1.903 Kg, 107%, contains residual ethyl acetate).

Workup

  1. washThe reaction was washed with water (2×4 L)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d937a26b5718461297132c0779be5910
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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