Trifluoroacetic acid → HCID 117599199, compound

HRID 522404Notes

Reaction equation

HRID 522404 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]3[O:25][C@H:26]4[CH2:49][N:29]([C:30](=[O:48])[C@H:31]([C:44]([CH3:47])([CH3:46])[CH3:45])[NH:32][C:33](=[O:43])[O:34][C@@H:35]5[CH2:42][C@H:36]5[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:16]=23)[C@H:28]([C:50]([O:52][CH3:53])=[O:51])[CH2:27]4)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:54][C:55]([F:60])([F:59])[C:56]([OH:58])=[O:57]>ClCCl>[F:54][C:55]([F:60])([F:59])[C:56]([OH:58])=[O:57].[C:44]([C@H:31]1[C:30](=[O:48])[N:29]2[CH2:49][C@@H:26]([CH2:27][C@H:28]2[C:50]([O:52][CH3:53])=[O:51])[O:25][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:15]([O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[C:16]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][C@@H:36]2[CH2:42][C@H:35]2[O:34][C:33](=[O:43])[NH:32]1)([CH3:47])([CH3:45])[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89590519HCID 89590519, compound

Product 1

HCID 117599199HCID 117599199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from step 1 in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The resulting solution was stirred for 1 hour at room temperature until disappearance of the starting material. The solvent was removed in vacuo. Purification of the residue by flash chromatography (ISCO reverse phase, 5 to 95% acetonitrile in water (0.5% TFA buffer)) gave the desired product (170 mg). LRMS (ES+) m/z 637.5 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification of the residue by flash chromatography (ISCO reverse phase, 5 to 95% acetonitrile in water (0.5% TFA buffer))

Sources & evidence

ORD record
ord-4418f952cf9e44beb2c1c87312bcc49b
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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