(2S,5S)-tert-butyl 2-[(2-amino-6-fluorophenoxy)methyl]-5-[(carbamoyloxy)methyl]morpholine-4-carboxylate → methyl N-[(1S,2S)-1-[[2-[[(2S,5S)-5-(carbamoyloxymethyl)morpholin-2-yl]methoxy]-3-fluoro-phenyl]carbamoyl]-2-(3-fluorophenyl)-2-(4-fluorophenyl)ethyl]carbamate

HRID 629785Notes

Reaction equation

HRID 629785 reaction equation
[N:1]([C@@H:4]([C@H:8]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:5]([OH:7])=O)=[N+]=[N-].[NH2:23][C:24]1[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[C:25]=1[O:26][CH2:27][C@H:28]1[O:33][CH2:32][C@@H:31]([CH2:34][O:35][C:36](=[O:38])[NH2:37])[N:30](C(OC(C)(C)C)=O)[CH2:29]1>>[C:36]([O:35][CH2:34][C@H:31]1[NH:30][CH2:29][C@@H:28]([CH2:27][O:26][C:25]2[C:46]([F:50])=[CH:47][CH:48]=[CH:49][C:24]=2[NH:23][C:5](=[O:7])[C@H:4]([C@H:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[NH:1][C:36]([O:35][CH3:34])=[O:38])[O:33][CH2:32]1)(=[O:38])[NH2:37]

Participants

3

Reactant 2

HCID 86726396(2S,5S)-tert-butyl 2-[(2-amino-6-fluorophenoxy)methyl]-5-[(carbamoyloxy)methyl]morpholine-4-carboxylateHCID 86726397(2S,3S)-2-Azido-3-(3-fluorophenyl)-3-(4-fluorophenyl)propanoic acid

Product 1

HCID 86578235methyl N-[(1S,2S)-1-[[2-[[(2S,5S)-5-(carbamoyloxymethyl)morpholin-2-yl]methoxy]-3-fluoro-phenyl]carbamoyl]-2-(3-fluorophenyl)-2-(4-fluorophenyl)ethyl]carbamate

Procedure

The title compound was prepared from the product of step 1 and the product of step 5 using the procedures given in steps 2-4 of Example 93. MS (ES) m/z=617 (M+H)+.

Sources & evidence

ORD record
ord-8ea4b68d962247c6a1245d334a635026
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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