Sodium Hydroxide → HCID 89726243, compound

HRID 926402Notes

Reaction equation

HRID 926402 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C@H:10]([NH:13][C:14]([C:16]2[N:24]3[C:19]([CH2:20][O:21][CH2:22][CH2:23]3)=[C:18]([C:25](=[O:36])[NH:26][C@@H:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][CH3:29])[CH:17]=2)=[O:15])[CH2:11][CH3:12])[CH:5]=1.COC(=O)C1C=CC=C([C@H](N)CC)C=1.[OH-].[Na+]>CO>[C:30]1([C@H:27]([NH:26][C:25]([C:18]2[CH:17]=[C:16]([C:14]([NH:13][C@@H:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:37])=[O:2])[CH2:11][CH3:12])=[O:15])[N:24]3[CH2:23][CH2:22][O:21][CH2:20][C:19]=23)=[O:36])[CH2:28][CH3:29])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 55253997HCID 55253997, compoundHCID 89726850HCID 89726850, compound

Product 1

HCID 89726243HCID 89726243, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-((R)-1-{[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-amino}-propyl)-benzoic acid methyl ester (synthesized from comp. no. 11a and 3-((R)-1-amino-propyl)-benzoic acid methyl ester) in methanol (0.5 ml) and 2 N aqueous sodium hydroxide (0.5 ml) was stirred at reflux for 1 h, the solvents were evaporated, water was added and the solution was acidified with excess aqueous hydrochloric acid. The solid formed was filtered off, washed with water and dried in vacuo to give 41 mg (73%) of 3-((R)-1-{[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-amino}-propyl)-benzoic acid. LC/MS (method 2): rt=1.1 min; m/z=490.4 (M+H+).

Workup

  1. temperatureat reflux for 1 h
  2. customthe solvents were evaporated
  3. additionwater was added
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-55bd946acb4b43cb948794518e430b5b
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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