Ethyl trifluoroacetate → HCID 86694602, compound

HRID 63312Notes

Reaction equation

HRID 63312 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([C:6]1[O:7][C:8](/[CH:11]=[CH:12]/[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][CH:10]=1)[OH:5].[F:19][C:20]([F:27])([F:26])[C:21](OCC)=[O:22]>C(Cl)Cl>[CH:13]1(/[CH:12]=[CH:11]/[C:8]2[O:7][C:6]([CH:4]([OH:5])[CH2:3][CH2:2][NH:1][C:21](=[O:22])[C:20]([F:27])([F:26])[F:19])=[CH:10][CH:9]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 86694603(E)-3-amino-1-(5-(2-cyclohexylvinyl)furan-2-yl)propan-1-ol

Product 1

HCID 86694602HCID 86694602, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-amino-1-(5-(2-cyclohexylvinyl)furan-2-yl)propan-1-ol (0.25 g, 1.0 mmol) was dissolved in CH2Cl2 (5 mL) and ethyl trifluoroacetate (0.5 mL) was added. The reaction mixture was stirred at room temperature for 30 min and concentrated under reduced pressure. Purification by flash chromatography (10%-50% EtOAc—hexanes gradient) gave (E)-N-(3-(5-(2-cyclohexylvinyl)furan-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide as a colorless oil. Yield (0.26 g, 75%). (E)-N-(3-(5-(2-Cyclohexylvinyl)furan-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide (0.15 g, 0.434 mmol) was dissolved in MeOH:H2O (3:1, 8 mL) and K2CO3 (0.13 g, 0.94 mmol) was added. The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. Flash chromatography purification (2%-16% 7N NH3/MeOH—CH2Cl2 gradient) gave Example 14 as a light yellow oil. Yield (0.025 g, 23%); 1H NMR (400 MHz, CD3OD) δ 6.00-6.40 (m, 4H), 4.64-4.74 (m, 1H), 2.70-2.80 (m, 2H), 2.01-2.14 (m, 1H), 1.90-2.00 (m, 2H), 1.50-1.80 (m, 5H), 1.10-1.40 (m, 5H); RP-HPLC tR=10.06 min; ESI-MS m/z 232.2 [M−H2O+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by flash chromatography (10%-50% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-7543c622144c4b9ba8399b470d3ca51c
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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