Ammonia → tert-Butyl 2-(3-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenethoxy)-N-cyclohexylpropanamido)ethyl(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

HRID 1255356Notes

Reaction equation

HRID 1255356 reaction equation
[CH:1]1([N:7]([CH2:39][CH2:40][N:41]([CH2:49][CH2:50][C:51]2[C:56]3[O:57][CH2:58][C:59](=[O:61])[NH:60][C:55]=3[C:54]([OH:62])=[CH:53][CH:52]=2)[C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:8](=[O:38])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]3[CH2:37][CH2:36][C:24]4([O:29][CH2:28][CH2:27][N:26](C(=O)C(F)(F)F)[CH2:25]4)[CH2:23][CH2:22]3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N>CO>[O:29]1[C:24]2([CH2:36][CH2:37][N:21]([CH2:20][C:16]3[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=3)[CH2:13][CH2:12][O:11][CH2:10][CH2:9][C:8]([N:7]([CH2:39][CH2:40][N:41]([CH2:49][CH2:50][C:51]3[C:56]4[O:57][CH2:58][C:59](=[O:61])[NH:60][C:55]=4[C:54]([OH:62])=[CH:53][CH:52]=3)[C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:45])[CH3:46])[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:38])[CH2:22][CH2:23]2)[CH2:25][NH:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58168563tert-Butyl 2-(N-cyclohexyl-3-(3-((4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanamido)ethyl(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

Product 1

HCID 58168531tert-Butyl 2-(3-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenethoxy)-N-cyclohexylpropanamido)ethyl(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-(N-cyclohexyl-3-(3-((4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanamido)ethyl(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate [Examples 81-175, step g] (1.1 g) in methanol (10 mL) was treated with 35% aqueous ammonia (2.5 mL) and stirred at room temperature for 4.25 hours, then concentrated in-vacuo to afford the subtitled compound as a pale yellow foam. Yield 0.97 g.

Workup

  1. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-dbf1582eed8245febffa93e5be6e456e
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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