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tert-Butyl N-[(10R,11E,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,11,15,17-heptaen-14-yl]carbamate → tert-Butyl N-[(10R,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamate

HRID 1481291
Notes
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Reaction equation

HRID 1481291 reaction equation
[CH3:1][C@H:2]1[C:3](=[O:29])[NH:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]2[CH:12]=[CH:13][N:14]=[C:15]([CH:28]=2)[C@@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17][CH:18]=[CH:19]1>CCOC(C)=O.[Pt](=O)=O>[CH3:1][C@@H:2]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:15]2[CH:28]=[C:11]([CH:12]=[CH:13][N:14]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][C:3]1=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 126739861tert-Butyl N-[(10R,11E,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,11,15,17-heptaen-14-yl]carbamate

Product 1

HCID 131736623tert-Butyl N-[(10R,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamateYield 97.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl Acetate
Solvent

Procedure

45F (974 mg, 2.475 mmol) in EtOAc (49.500 mL) was added platinum(IV) oxide (56.2 mg, 0.248 mmol). The reaction mixture was charged with H2 balloon and vacuum/H2 several times. The reaction was stirred at rt under H2 overnight. The reaction was filtered and concentrated to give the desired product (0.95 g, 97%) as a brownish solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 8.68 (d, J=5.0 Hz, 1H), 7.47-7.30 (m, 5H), 7.26-7.22 (m, 1H), 6.79 (br. s., 1H), 5.85 (d, J=7.7 Hz, 1H), 4.74 (br. s., 1H), 2.52-2.42 (m, 1H), 2.18-2.07 (m, 1H), 1.66-1.57 (m, 1H), 1.51-1.46 (m, 1H), 1.43 (s, 9H), 1.40-1.33 (m, 1H), 1.07 (br. s., 1H), 1.00 (d, J=6.9 Hz, 3H), 0.83 (d, J=9.9 Hz, 1H). MS (ESI) m/z: 396.2 (M+H)+.

Workup

  1. additionThe reaction mixture was charged with H2 balloon and vacuum/H2 several times
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-330d741a956241f489300129d1885e1b
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409908B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes