Sodium Hydroxide → HCID 68587833, compound

HRID 1819289Notes

Reaction equation

C([O:3][C:4]([C@@H:6]1[CH2:15][C@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([O:16][C:17]3[CH:22]=[C:21]([N:23]4[CH:27]=[CH:26][CH:25]=[N:24]4)[CH:20]=[CH:19][C:18]=3[C:28]3[N:29]=[N:30][NH:31][N:32]=3)[CH2:13]2)[CH2:8][N:7]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:5])C.[OH-].[Na+]>CO>[C:36]([O:35][C:33]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([O:16][C:17]3[CH:22]=[C:21]([N:23]4[CH:27]=[CH:26][CH:25]=[N:24]4)[CH:20]=[CH:19][C:18]=3[C:28]3[N:29]=[N:30][NH:31][N:32]=3)[CH2:13]2)[CH2:8]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

Conditions

Temperature: 50 °C

Procedure

To 0.129 g of the material from Step B, above, dissolved in 10 mL MeOH is added 0.72 mL 1N NaOH. The reaction is heated to 50° C. overnight. 0.72 mL 1N NaOH is then added and heated for four more hours. Upon completion, the reaction is concentrated in vacuo, redissolved in water and acidified to pH 3, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography eluting with 10% MeOH/CHCl3 provides 0.040 g of the title compound (32.8% yield), which is used directly in the following step.

Workup

temperatureheated for four more hours
concentrationUpon completion, the reaction is concentrated in vacuo
dissolutionredissolved in water
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washFlash chromatography eluting with 10% MeOH/CHCl3

Sources & evidence

ORD record: ord-2975b9df52c4496a99c8580df9f15348
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601738B2

Reaction notes

Loading…