HCID 86679587, compound → HCID 71542648, compound

HRID 1776641Notes

Reaction equation

HRID 1776641 reaction equation
C(OC([NH:8][C@H:9]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:10]([O:12][C@H:13]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[CH:25]=1)[CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][N+:18]([O-:22])=[CH:17][C:16]=1[Cl:23])=[O:11])=O)(C)(C)C>Cl.CCOC(C)=O>[NH2:8][C@H:9]([CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:10]([O:12][C@H:13]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[CH:25]=1)[CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][N+:18]([O-:22])=[CH:17][C:16]=1[Cl:23])=[O:11]

Participants

4

Reactant 1

HCID 86679587HCID 86679587, compound

Product 1

HCID 71542648HCID 71542648, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-((S)-2-((R)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (2.9 g, 4.34 mmol) was dissolved in HCl 4M in EtOAc (15 ml). The reaction was stirred at RT for 30 minutes. A precipitate formed, and it was filtered and dried in the vacuum oven to give 4-((S)-2-((R)-2-amino-3-phenylpropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide as an hydrochloride salt. (2 g, 3.52 mmol, 81% yield).

Workup

  1. customA precipitate formed
  2. filtrationit was filtered
  3. customdried in the vacuum oven

Sources & evidence

ORD record
ord-38301c154e374e95a82ec8515fd29c89
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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