Trifluoroacetic acid → HCID 86705895, compound

HRID 339256Notes

Reaction equation

HRID 339256 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:63]([CH3:66])([CH3:65])[CH3:64])[C:13]([N:15]1[C@H:19]([C:20](=[O:32])[NH:21][C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)[CH2:18][C@H:17]([C:33]2[CH:42]=[C:41]3[C:36]([CH2:37][C@@H:38]([C:50](=[O:62])[NH:51][C@H:52]4[C:61]5[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=5)[CH2:55][CH2:54][CH2:53]4)[N:39](C(OC(C)(C)C)=O)[CH2:40]3)=[CH:35][CH:34]=2)[CH2:16]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCCl>[CH3:64][C:63]([CH3:66])([CH3:65])[C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:13](=[O:14])[N:15]1[CH2:16][C@@H:17]([C:33]2[CH:42]=[C:41]3[C:36]([CH2:37][C@@H:38]([C:50](=[O:62])[NH:51][C@H:52]4[C:61]5[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=5)[CH2:55][CH2:54][CH2:53]4)[NH:39][CH2:40]3)=[CH:35][CH:34]=2)[CH2:18][C@H:19]1[C:20](=[O:32])[NH:21][C@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705896HCID 86705896, compound

Product 1

HCID 86705895HCID 86705895, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (S)-tert-butyl 7-((3R,5S)-1-((S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.44 g, 0.49 mmol) in DCE (5 mL) was added TFA (1.2 mL, 15.6 mmol). The reaction mixture was stirred at rt for 2 h and concentrated in vacuo. The residue was basified with sat. aq. NaHCO3 solution. The resulting mixture was extracted with EtOAc (2×) and the organic layer was separated, washed with brine and dried over MgSO4. The filtrate was concentrated in vacuo to give the title compound as a light yellow solid (0.35 g, 91%). MS (ESI+) m/z 796.5 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe resulting mixture was extracted with EtOAc (2×)
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a17ed006d40f46fb895228b91dc8f459
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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