Trifluoroacetic acid → HCID 67075982, compound

HRID 909896Notes

Reaction equation

HRID 909896 reaction equation
C(OC([O:8][C:9]1[C:18]2[NH:17][C:16](=[O:19])[CH2:15][O:14][C:13]=2[C:12]([CH2:20][CH2:21][N:22]([CH2:30][CH2:31][N:32]([CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)[C:33](=[O:51])[CH2:34][CH2:35][O:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]3[N:46]=[N:47][N:48]([CH3:50])[CH:49]=3)[CH:40]=2)C(=O)OC(C)(C)C)=[CH:11][CH:10]=1)=O)(C)(C)C.[C:58]([OH:64])([C:60]([F:63])([F:62])[F:61])=[O:59]>C(Cl)Cl>[F:61][C:60]([F:63])([F:62])[C:58]([OH:64])=[O:59].[CH:52]1([N:32]([CH2:31][CH2:30][NH:22][CH2:21][CH2:20][C:12]2[C:13]3[O:14][CH2:15][C:16](=[O:19])[NH:17][C:18]=3[C:9]([OH:8])=[CH:10][CH:11]=2)[C:33](=[O:51])[CH2:34][CH2:35][O:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]3[N:46]=[N:47][N:48]([CH3:50])[CH:49]=3)[CH:40]=2)[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67390595HCID 67390595, compound

Product 1

HCID 67075982HCID 67075982, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 2-(5-(tert-butoxycarbonyloxy)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl(2-(N-cyclohexyl-3-(3-(1-methyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamido)ethyl)carbamate [Example 5, Step iv)] (290 mg), DCM (5 mL) and TFA (2.5 mL) was stirred at 25° C. for 30 min. The reaction mixture was evaporated to afford crude product. The crude product was purified by preparative HPLC on a Phenomenex Gemini column using a 15-60% gradient of aqueous 0.1% trifluoroacetic acid in acetonitrile as eluent to afford the titled compound as a white solid (94 mg). MS [M+H]+=591.3 (calc=591.3295) (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.21 (s, 1H), 7.69 (s, 1H), 7.57 (dt, J=1.6 and 8.0 Hz, 1H), 7.32 (t, J=7.6 Hz, 1H), 7.19 (d, J=7.6 Hz, 1H), 6.69 (d, J=8.2 Hz, 1H), 6.47 (d, J=8.5 Hz, 1H), 4.60 (s, 2H), 4.12 (s, 3H), 3.75-3.64 (m, 5H), 3.52-3.44 (m, 2H), 3.12 (t, J=7.3 Hz, 2H), 3.02 (t, J=5.6 Hz, 2H), 2.88 (t, J=6.7 Hz, 2H), 2.86 (t, J=7.0 Hz, 2H), 2.63 (t, J=5.9 Hz, 2H), 1.80-1.72 (m, 2H), 1.69-1.58 (m, 2H), 1.46-1.24 (m, 5H), 1.15-1.03 (m, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. customto afford crude product
  3. customThe crude product was purified by preparative HPLC on a Phenomenex Gemini column

Sources & evidence

ORD record
ord-15a737fd16624b7c961e0c18c24adc8b
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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