Diethyl Ether → 2,3-Dihydroxybutanedioate

HRID 2375073Notes

Reaction equation

HRID 2375073 reaction equation
[CH3:1][N:2]([CH3:34])[C@@H:3]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:25](=[O:26])[NH:24][N:23]=[CH:22][C:11]3=[C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][C:14]([CH:15]=1)=[C:10]23)=[O:5].C(OCC)C.CCCCCC.[C:46]([OH:55])(=[O:54])[C@@H:47]([C@H:49]([C:51]([OH:53])=[O:52])[OH:50])[OH:48]>CO.O1CCCC1>[OH:50][C@H:49]([C@@H:47]([OH:48])[C:46]([OH:55])=[O:54])[C:51]([OH:53])=[O:52].[CH3:34][N:2]([CH3:1])[C@@H:3]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:25](=[O:26])[NH:24][N:23]=[CH:22][C:11]3=[C:12]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:13][C:14]([CH:15]=1)=[C:10]23)=[O:5].[C:51]([CH:49]([CH:47]([C:46]([O-:55])=[O:54])[OH:48])[OH:50])([O-:53])=[O:52]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 444305L-Tartaric acidHCID 136141672HCID 136141672, compound

Product 2

HCID 38061142,3-DihydroxybutanedioateYield 200%HCID 136395586HCID 136395586, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

One batch of freebase (S)-2-Dimethylamino-N-(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-3-phenyl-propionamide (22 mg, 0.049 mmol) from Example 71a was triturated with 1:1 diethyl ether:hexane giving purified material (20 mg, 0.044 mmol). A portion (10 mg, 0.022 mmol) was then dissolved in a small amount of c.a. 1:1 tetrahydrofuran:methanol and treated with L-tartaric acid (3.3 mg, 0.022 mmol). The volatile components of the resulting clear solution were removed under a stream of argon. To the resulting yellow oil was added diethyl ether plus one drop of methanol giving a fine yellow precipitate which was isolated by decanting most of the liquid and subsequent high vacuum removal of the remaining volatile components to afford the title compound as a tartrate salt (13 mg, 0.022 mmol) in quantitative yield.

Workup

  1. dissolutionA portion (10 mg, 0.022 mmol) was then dissolved in a small amount of c.a
  2. customThe volatile components of the resulting clear solution were removed under a stream of argon
  3. additionTo the resulting yellow oil was added diethyl ether plus one drop of methanol giving a fine yellow precipitate which
  4. customwas isolated
  5. customby decanting most of the liquid and subsequent high vacuum removal of the remaining volatile components

Sources & evidence

ORD record
ord-a94b4f3fdd434c86a627ae512a5f7415
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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