Benzyl bromoacetate → HCID 178482583, compound

HRID 347901Notes

Reaction equation

HRID 347901 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]1[C:23]2[CH2:22][C@@H:21]3[C:12](=[C:13]([OH:33])[C@@:14]4([OH:32])[C@@H:19]([CH2:20]3)[C@H:18]([N:24]([CH3:26])[CH3:25])[C:17]([OH:27])=[C:16]([C:28]([NH2:30])=[O:29])[C:15]4=[O:31])[C:11](=[O:34])[C:10]=2[C:9]2[O:8][C:7](=[S:35])[NH:6][C:5]=2[CH:4]=1.C(N(C(C)C)CC)(C)C.[CH2:46]([O:53][C:54](=[O:57])[CH2:55]Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C)C=O>[NH2:30][C:28]([C:16]1[C:15](=[O:31])[C@:14]2([OH:32])[C@@H:19]([CH2:20][C@H:21]3[C:12](=[C:13]2[OH:33])[C:11](=[O:34])[C:10]2[C:9]4[O:8][C:7]([S:35][CH2:55][C:54]([O:53][CH2:46][C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)=[O:57])=[N:6][C:5]=4[CH:4]=[C:3]([N:2]([CH3:36])[CH3:1])[C:23]=2[CH2:22]3)[C@H:18]([N:24]([CH3:25])[CH3:26])[C:17]=1[OH:27])=[O:29]

Participants

5

Reactant 3

HCID 62576Benzyl bromoacetateHCID 81531DiisopropylethylamineHCID 178482585HCID 178482585, compound

Product 1

HCID 178482583HCID 178482583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (6aR,7aS,8S,11aS)-5,8-bis(dimethylamino)-9,11a,12-trihydroxy-11,13-dioxo-2-thioxo-2,3,6,6a,7,7a,8,11,11a,13-decahydrotetraceno[2,1-d][1,3]oxazole-10-carboxamide (Example 42) in N,N-dimethylformamide (DMF) is added 2 equivalents of diisopropylethylamine, after stirring for 5 min. 1.2 equivalent of benzyl-2-bromoacetate is added. The reaction mixture is stirred for 1 hr and mixture triturated with diethyl ether and solid is collected. It is purified by extraction.

Workup

  1. stirringThe reaction mixture is stirred for 1 hr
  2. custommixture triturated with diethyl ether and solid
  3. customis collected
  4. customIt is purified by extraction

Sources & evidence

ORD record
ord-2e2d55facfcd48f48f4e1802294e8a3c
Source dataset
uspto-grants-2007_02
Patent number
US07176225B2

Reaction notes

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