Lithium Hydroxide → HCID 22876403, compound

HRID 1585358Notes

Reaction equation

HRID 1585358 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([CH3:32])[C:25]=2[CH3:33])[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:34].[Li+]>C(COC)OC.O.[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([CH3:32])[C:25]=1[CH3:33])[C:20]([OH:22])=[O:34])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 70149816HCID 70149816, compound

Product 1

HCID 22876403HCID 22876403, compound

Reagents, catalysts & solvents 4

HCID 311Citric AcidSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 1.001 g (2.2 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,3-dimethyl-4-methoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 35.8 ml of dimethoxyethane and 18 ml of water is treated, at RT, with 8.8 ml of a 1M solution of lithium hydroxide in water, and this reaction mixture is stirred for 2.5 h. It is then transferred to a separating funnel and diluted with 108.5 ml of sat. ammonium chloride solution and 9 ml of a 10% citric acid solution (both being cold); the whole is then extracted with ethyl acetate and a little THF. The title compound, which is subjected to further processing without being purified, is obtained after washing the organic phase with (cold) saline and drying it over sodium sulfate. TLC Rf (hexane:ethyl acetate 1:1)=at the start. FAB-MS (M+H)+ =472; IR(KBr) inter alia: 1724, 1666, 1527 and 1169 cm-1. 1H-NMR(CD3OD) inter alia: 7.31-7.11 (m, 5H); 6.93 and 6.68 (each d, each 1H); 3.76 (s, 3H); 3.23 and 2.59 (each dxd, each 1H); 2.21 and 2.12 (each s, each 3H); 1.27 (s, 9H).

Workup

  1. customIt is then transferred to a separating funnel
  2. extractionthe whole is then extracted with ethyl acetate
  3. customwithout being purified
  4. customis obtained
  5. washafter washing the organic phase with (cold) saline
  6. dry with materialdrying it over sodium sulfate

Sources & evidence

ORD record
ord-bf95ffc3e9b54ff08b0d92fbe386fa01
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

Loading…