Diisopropylethylamine → methyl-[(S)-1-((6S,7S)-6-methyl-8-oxo-2-trifluoromethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1055446Notes

Reaction equation

HRID 1055446 reaction equation
CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[NH2:17][C@H:18]1[C@H:24]([CH3:25])[O:23][C:22]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][C:21]=2[NH:20][C:19]1=[O:34].[C:35]([O:39][C:40]([N:42]([CH3:48])[C@@H:43]([CH3:47])[C:44](O)=[O:45])=[O:41])([CH3:38])([CH3:37])[CH3:36]>>[C:35]([O:39][C:40](=[O:41])[N:42]([CH3:48])[C@H:43]([C:44](=[O:45])[NH:17][C@@H:18]1[C:19](=[O:34])[NH:20][C:21]2[CH:29]=[C:28]([C:30]([F:31])([F:33])[F:32])[CH:27]=[CH:26][C:22]=2[O:23][C@H:24]1[CH3:25])[CH3:47])([CH3:36])([CH3:38])[CH3:37]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 90037733HCID 90037733, compound

Product 1

HCID 90037194methyl-[(S)-1-((6S,7S)-6-methyl-8-oxo-2-trifluoromethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl esterYield 75.3%

Procedure

In a similar manner to that described for Example 36 Step 1 except 4 equivalents of DIEA were used, (2S,3S)-3-amino-2-methyl-7-(trifluoromethyl)-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one trifluoroacetate (58 mg, 0.155 mmol) and (S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid (31.5 mg, 155 μmol) were converted to a material which was purified by silica gel chromatography to afford methyl-[(S)-1-((6S,7S)-6-methyl-8-oxo-2-trifluoromethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (52 mg, 75%)

Workup

  1. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3aacd9e608e24de7856ce030b61496d5
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…