Ammonia methanol dichloromethane → HCID 86694605, compound

HRID 63314Notes

Reaction equation

HRID 63314 reaction equation
[CH:1]1([CH2:7][CH2:8][CH:9]2[O:13][CH:12]([CH:14]([OH:24])[CH2:15][CH2:16][NH:17]C(=O)C(F)(F)F)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N.CO.C(Cl)Cl>>[NH2:17][CH2:16][CH2:15][CH:14]([CH:12]1[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:13]1)[OH:24]

Participants

3

Reactant 2

HCID 21584172Ammonia methanol dichloromethaneHCID 86694604HCID 86694604, compound

Product 1

HCID 86694605HCID 86694605, compound

Procedure

Deprotection of N-(3-(5-(2-cyclohexylethyl)tetrahydrofuran-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide following the method used in Example 14 gave after flash chromatography purification (4%-16% 7N NH3/MeOH—CH2Cl2 gradient) Example 15 as a colorless oil. Yield (0.033 g, 40%); 1H NMR (400 MHz, CD3OD) δ 3.62-3.84 (m, 2H), 3.45-3.57 (m, 2H), 2.71-2.88 (m, 2H), 1.80-2.05 (m, 2H), 1.39-1.80 (m, 10H), 1.09-1.37 (m, 6H), 0.87-0.99 (m, 2H); RP-HPLC tR=9.75 min; ESI-MS m/z 256.3 [M+H]+.

Workup

  1. customgave
  2. customYield (0.033 g, 40%)

Sources & evidence

ORD record
ord-9a57749e02cf43eaa0b32fdeb8f869d3
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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