Ethyl trifluoroacetate → 3-(2,2,2-trifluoro-acetylamino)-oxetane-3-carboxylic acid ((S)-5-bromo-indan-1-yl)-amide

HRID 2046534Notes

Reaction equation

HRID 2046534 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([NH2:11])[CH2:6][CH2:5]2.[F:12][C:13]([F:25])([F:24])[C:14]([NH:16][C:17]1([C:21](O)=[O:22])[CH2:20][O:19][CH2:18]1)=[O:15].NC1(C(O)=O)COC1.C(OC(=O)C(F)(F)F)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([NH:11][C:21]([C:17]1([NH:16][C:14](=[O:15])[C:13]([F:25])([F:12])[F:24])[CH2:18][O:19][CH2:20]1)=[O:22])[CH2:6][CH2:5]2

Participants

5

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 150242563-Aminooxetane-3-carboxylic acidHCID 28206724(S)-5-bromo-2,3-dihydro-1H-inden-1-amineHCID 866757743-(2,2,2-Trifluoro-acetylamino)-oxetane-3-carboxylic acid

Product 1

HCID 866757733-(2,2,2-trifluoro-acetylamino)-oxetane-3-carboxylic acid ((S)-5-bromo-indan-1-yl)-amide

Procedure

In analogy to the procedure described for the preparation of intermediate A-1 [B] and A-1 [C], (S)-5-bromo-indan-1-ylamine has been coupled with 3-(2,2,2-trifluoro-acetylamino)-oxetane-3-carboxylic acid (prepared from 3-amino-oxetane-3-carboxylic acid and trifluoro-acetic acid ethyl ester in analogy to the procedure described for the preparation of intermediate A-1 [A]) to give 3-(2,2,2-trifluoro-acetylamino)-oxetane-3-carboxylic acid ((S)-5-bromo-indan-1-yl)-amide, which was subsequently reacted with 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) to yield the title compound as dark brown viscous oil. MS: 453.3 (M−H−).

Workup

  1. customdescribed for the preparation of intermediate A-1 [A])

Sources & evidence

ORD record
ord-079fcaa1ed4e4c4e856fd9356f8e4ea4
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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