HCID 89544762, compound → HCID 89544746, compound

HRID 2283402Notes

Reaction equation

C(OC(=O)[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18](=[O:34])[C:19]2[CH:24]=[CH:23][C:22]([C:25](C)(C)[O:26][SiH2]C(C)(C)C)=[CH:21][CH:20]=2)[C:12]=1[F:35])[CH2:9][CH3:10])(C)(C)C.N[C@@H](C1C(F)=[C:43]([C:48](C2C=CC(CO)=CC=2)=[O:49])C(Cl)=CC=1)CC>>[NH2:7][C@@H:8]([C:11]1[C:12]([F:35])=[C:13]([C:14]([Cl:17])=[CH:15][CH:16]=1)[C:18]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][O:26][C:48](=[O:49])[CH3:43])=[CH:23][CH:24]=1)=[O:34])[CH2:9][CH3:10]

Participants

Reactant 2

HCID 89544762HCID 89544762, compound

HCID 131733519HCID 131733519, compound

Product 1

HCID 89544746HCID 89544746, compound

Procedure

Step 2 ((R)-1-{3-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-benzoyl]-4-chloro-2-fluoro-phenyl}-propyl)-carbamic acid tert-butyl ester was deprotected as Step 2 in the preparation of Example 2. A mixture of the doubly deprotected product [3-((R)-1-amino-propyl)-6-chloro-2-fluoro-phenyl]-(4-hydroxymethyl-phenyl)-methanone (=Example 50) and the trans-esterified product acetic acid 4-[3-((R)-1-amino-propyl)-6-chloro-2-fluoro-benzoyl]-benzyl ester (=Example 49) was obtained. Separation was achieved by column chromatography with 0-8% ammonia in methanol/dichloromethane.

Sources & evidence

ORD record: ord-ad7fa68ca2934e549743ef958a6a93ea
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145354B2

Reaction notes

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