Lithium Hydroxide → HCID 22876403, compound

HRID 1377190Notes

Reaction equation

HRID 1377190 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 d×d, 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-93f61925bb6147519ab1740214ad5cc4
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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