Trifluoroacetic acid → HCID 117598881, compound

HRID 522413Notes

Reaction equation

HRID 522413 reaction equation
[CH:1]1([C@H:7]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:64][CH2:63]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:19]3=[N:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:27]([O:28][CH:29]4[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]4)=[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]3[CH2:68][C@H:11]3[O:10][C:9](=[O:69])[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:70][C:71]([F:76])([F:75])[C:72]([OH:74])=[O:73]>ClCCl>[F:70][C:71]([F:76])([F:75])[C:72]([O-:74])=[O:73].[CH:1]1([C@H:7]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:63][CH2:64]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:19]3=[N:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:27]([O:28][CH:29]4[CH2:30][CH2:31][NH2+:32][CH2:33][CH2:34]4)=[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]3[CH2:68][C@H:11]3[O:10][C:9](=[O:69])[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 76325272HCID 76325272, compound

Product 1

HCID 117598881HCID 117598881, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 235 (100 mg, 0.103 mmol) in dichloromethane (5 ml) was added trifluoroacetic acid (1.025 ml, 0.103 mmol). The reaction was stirred at room temperature for 2 hours at which stage LCMS indicated complete hydrolysis of the NBoc group. The volatiles were evaporated under reduced pressure and the residue was diluted with DCM and azeotroped twice with toluene. The resulting residue (˜101 mg) was dried under vacuum and used for the next step without purification.

Workup

  1. customhydrolysis of the NBoc group
  2. customThe volatiles were evaporated under reduced pressure
  3. additionthe residue was diluted with DCM
  4. customazeotroped twice with toluene
  5. dry with materialThe resulting residue (˜101 mg) was dried under vacuum
  6. customused for the next step without purification

Sources & evidence

ORD record
ord-d5b34c7d20a64351ba6c6734b56d970f
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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