Trifluoroacetic acid methylene chloride → HCID 66849684, compound

HRID 254391Notes

Reaction equation

HRID 254391 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH:12]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:13][CH2:14][CH2:15][N:16]([CH2:24][C@H:25]([OH:30])[C@H:26]([OH:29])[CH2:27][OH:28])[CH2:17][C@H:18]([OH:23])[C@H:19]([OH:22])[CH2:20][OH:21])=O)(C)(C)C.ClCCl.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>>[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41].[OH:23][C@H:18]([C@H:19]([OH:22])[CH2:20][OH:21])[CH2:17][N:16]([CH2:15][CH2:14][NH:13][CH:12]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:11][CH2:10][CH2:9][NH2:8])[CH2:24][C@H:25]([OH:30])[C@H:26]([OH:29])[CH2:27][OH:28]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66850058HCID 66850058, compound

Product 1

HCID 66849684HCID 66849684, compoundYield 98%

Procedure

The protected amine 760 (0.12 g, 0.22 mmol) was stirred in a mixture of dichloromethane/TFA (10 mL, 1:1) for 2 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, chloroform/methanol/ammonium hydroxide, 3:1:0.3, v/v) to provide 770 (0.12 g, 98%) as a colorless oil. (300 MHz, CD3OD) δ δ 1.64 (m, 4H), 2.55 (m, 2H), 2.90 (m, 2H), 3.45 (m, 4H), 3.60 (m, 10H), 3.97 (m, 2H), 6.67 (d, 2H), 7.00 (d, 2H). m/z (APCI) 416 [C20H37N3O6+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, chloroform/methanol/ammonium hydroxide, 3:1:0.3

Sources & evidence

ORD record
ord-c83706d1b4ad4edea4738798014e9028
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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