Hydrochloric Acid → (R)-1-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid

HRID 926397Notes

Reaction equation

HRID 926397 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([C:12]1[N:20]2[C:15]([CH2:16][O:17][CH2:18][CH2:19]2)=[C:14]([C:21](=[O:32])[NH:22][C@@H:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH3:25])[CH:13]=1)=[O:11])=[O:4].COC(C1CCCN1C(C1N2C(COCC2)=C(C(=O)N[C@@H](C2C=CC=CC=2)CC)C=1)=O)=O.[OH-].[Na+].Cl>O1CCCC1.O>[C:26]1([C@H:23]([NH:22][C:21]([C:14]2[CH:13]=[C:12]([C:10]([N:6]3[CH2:7][CH2:8][CH2:9][C@@H:5]3[C:3]([OH:4])=[O:2])=[O:11])[N:20]3[CH2:19][CH2:18][O:17][CH2:16][C:15]=23)=[O:32])[CH2:24][CH3:25])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89726390(R)-1-[8-((R)-1-phenyl-propylcarbamoyI)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid methyl esterHCID 1265144481-[8-((R)-1-Phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 89726399(R)-1-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester (Comp. No. 16m) (171 mg, 0.389 mmol) in tetrahydrofuran (5 ml) and water (4 ml), and 2 M aqueous sodium hydroxide (1 ml, 2 mmol) was refluxed for 3 h, cooled to room temperature, acidified with excess aqueous hydrochloric acid, and extracted with dichloromethane. Solvents were evaporated to give 140 mg of (R)-1-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid.

Workup

  1. extractionextracted with dichloromethane
  2. customSolvents were evaporated

Sources & evidence

ORD record
ord-6b61ad6808c0440e94e00b34c1bf16bf
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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