Trifluoroacetic acid → HCID 131736352, compound

HRID 1055428Notes

Reaction equation

HRID 1055428 reaction equation
C(OC([N:8]([CH3:51])[C@@H:9]([CH3:50])[C:10]([NH:12][C@H:13]1[C:19]2([CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[O:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[N:15]([CH2:29][C:30]2[C:39](OC)=[CH:38][CH:37]=[C:36]3[C:31]=2[CH:32]=[CH:33][C:34]([C:42]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[O:43])=[CH:35]3)[C:14]1=[O:49])=[O:11])=O)(C)(C)C.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]>C(Cl)Cl>[F:55][C:54]([F:57])([F:56])[C:52]([OH:58])=[O:53].[CH2:52]([O:53][C:35]1[C:36]2[C:31](=[C:30]([CH2:29][N:15]3[C:14](=[O:49])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][CH3:51])[CH3:50])[C:19]4([CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[O:18][C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]3=4)[CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:33][C:34]=1[C:42]([NH:44][S:45]([CH3:48])(=[O:46])=[O:47])=[O:43])[CH3:54]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118574205HCID 118574205, compound

Product 1

HCID 131736352HCID 131736352, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(((S)-3-((S)-2-(tert-Butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-N-(methylsulfonyl)-2-naphthamide dissolved in DCM (1 mL) and 0.25 mL TFA was added. After 90 min the mixture was concentrated, the residue was dissolved in MeCN/H2O, and lyophilized to afford the title compound (45.4 mg, 67%) as a white solid. MS m/z 625.4 (MH+)

Workup

  1. concentrationAfter 90 min the mixture was concentrated
  2. dissolutionthe residue was dissolved in MeCN/H2O

Sources & evidence

ORD record
ord-a429ba17d18f453cbc216b187aff748c
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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