Hydrochloric Acid → tert-butyl (R)-4-carboxymethyl-3-(3,5-difluoro-phenyl)-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate

HRID 1615735Notes

Reaction equation

HRID 1615735 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18]C)=[O:17])[C:13](=[O:20])[C:12]3([CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21]3)[N:11]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C1COCC1.[OH-].[Li+].Cl>O>[C:16]([CH2:15][N:14]1[C:13](=[O:20])[C:12]2([CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26]2)[N:11]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:9]1[C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68154574tert-butyl (R)-3-(3,5-difluoro-phenyl)-4-methoxycarbonylmethyl-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate

Product 1

HCID 68154191tert-butyl (R)-4-carboxymethyl-3-(3,5-difluoro-phenyl)-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.235 g (0.50 mmol) tert-butyl (R)-3-(3,5-difluoro-phenyl)-4-methoxycarbonylmethyl-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate, 5 ml THF, 1 ml of water and 13.2 mg (0.55 mmol) lithium hydroxide were stirred for 2 h at RT. Then the mixture was adjusted to pH7 with a 0.1N hydrochloric acid. The reaction mixture was evaporated to dryness by rotary evaporation.

Workup

  1. customThe reaction mixture was evaporated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-d1f8f7c5a5804a8fb547e8868b59e752
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

Loading…