Sodium Hydroxide → HCID 86745756, compound

HRID 1195379Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:9]([C:25]2[N:29]([CH3:30])[N:28]=[N:27][N:26]=2)[CH:10]=[CH:11][C@@H:12]([OH:24])[CH2:13][C@@H:14]([OH:23])[CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])=[CH:4][CH:3]=1.[OH-].[Na+:39]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[C:9]([C:25]2[N:29]([CH3:30])[N:28]=[N:27][N:26]=2)[CH:10]=[CH:11][C@@H:12]([OH:24])[CH2:13][C@@H:14]([OH:23])[CH2:15][C:16]([O-:18])=[O:17])=[CH:6][CH:7]=1.[Na+:39]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of the dihydroxyester prepared in Step D (35 mg; 0.068 mmole) in ethanol (2 mL) was treated with 1N NaOH solution (68 l; 0.068 mmole) and the mixture stirred for 30 minutes at 23° C. The solvent was removed by evaporation in vacuo and the residue dissolved in water (2 mL) and lyophilized to afford 36 mg (100%) of the title compound; m.p.>110° C. decomp. [α]D25 =-22.2° (c=0.32, H2O). The 1H NMR and 13C NMR are identical to the (±)-erythro product prepared in Example 12.

Workup

customThe solvent was removed by evaporation in vacuo
dissolutionthe residue dissolved in water (2 mL)

Sources & evidence

ORD record: ord-a06b2c6baf5e40e59ab92861412297ce
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05110940

Reaction notes

Loading…