Water → HCID 58124931, compound

HRID 1971683Notes

Reaction equation

HRID 1971683 reaction equation
[CH:1]([N:4]1[C:30](=[O:31])[C:29]2[N:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[C:17]([O:27][CH3:28])[C:18]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[CH:19][C:20]=4[C:11]3=[C:10]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:9]=2[CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:37][C:38](OC(C)=O)=[O:39].O.[NH4+].[OH-]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:38]([N:7]1[CH2:8][C:9]2[C:10]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[C:11]3[C:20]4[CH:19]=[C:18]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)[C:17]([O:27][CH3:28])=[CH:16][C:15]=4[CH2:14][CH2:13][N:12]3[C:29]=2[C:30](=[O:31])[N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]1)(=[O:39])[CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 58124899HCID 58124899, compound

Product 1

HCID 58124931HCID 58124931, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 32 mg of 10n in 200 μl of pyridine was treated with 30 μl of Ac2O and 1 mg of DMAP and was stirred at RT for 1 hr. Then, 2 ml of water was added and stirring was continued for 1 hr at RT. The mixture was made slightly alkaline by addition of conc. aq. NH4OH and was extracted with ethyl acetate. The organic layer was washed with a small amount of sat. NaCl, dried, concentrated and treated with diisopropyl ether, to give 30 mg of white crystalline 10p. Mp: 225-226° C.; Rf 0.40 (CH2Cl2/acetone 1/1). MS-ESI: [M+1] 541.12.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hr at RT
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with a small amount of sat. NaCl
  5. customdried
  6. concentrationconcentrated
  7. additiontreated with diisopropyl ether

Sources & evidence

ORD record
ord-e493790c281e4d739d78b69add1e5ac4
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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