Trifluoroacetic acid → HCID 72712974, compound

HRID 1055426Notes

Reaction equation

HRID 1055426 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(O[C:13]([N:15](C)[C@@H:16]([CH3:53])[C:17]([NH:19][C@H:20]1[C:26]2([CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[O:25][C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[N:22]([CH2:36][C:37]2[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[C:43]3[C:38]=2[CH:39]=[CH:40][C:41]([C:49]([OH:51])=[O:50])=[CH:42]3)[C:21]1=[O:52])=[O:18])=O)(C)(C)C>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[CH3:48][O:47][C:46]1[C:37]([CH2:36][N:22]2[C:21](=[O:52])[C@@H:20]([NH:19][C:17](=[O:18])[C@@H:16]([NH:15][CH3:13])[CH3:53])[C:26]3([CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[O:25][C:24]3[CH:32]=[CH:33][CH:34]=[CH:35][C:23]2=3)=[C:38]2[C:43](=[CH:44][CH:45]=1)[CH:42]=[C:41]([C:49]([OH:51])=[O:50])[CH:40]=[CH:39]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736350HCID 131736350, compound

Product 1

HCID 72712974HCID 72712974, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.2 mL, 56.4 μmol, Eq: 1.00) was added to a solution of 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-2-nap hthoic acid (36.5 mg, 56.4 μmol, Eq: 1.00) in DCM (1 mL). After 1 h, the mixture was concentrated, the residue dissolved in MeCN/H2O, and lyophilized to afford the title compound (31.0 mg, 83%) as an off-white solid. MS m/z 548.4 (MH+)

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue dissolved in MeCN/H2O

Sources & evidence

ORD record
ord-972f219f74434fbcb217c75513624cd3
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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