Cesium carbonate → HCID 54095865, compound

HRID 2187921Notes

Reaction equation

HRID 2187921 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]1[CH2:18][CH2:17][C:16]2[S:19][C:20]([NH:25][C:26]([O:28][CH2:29][CH:30]3[C:42]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:36]4[C:31]3=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:27])=[C:21]([C:22]([OH:24])=[O:23])[C:15]=2[O:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH:13]1[O:14][CH2:15][C:16]2[S:19][C:20]([NH:25][C:26]([O:28][CH2:29][CH:30]3[C:42]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:36]4[C:31]3=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:27])=[C:21]([C:22]([OH:24])=[O:23])[C:17]=2[CH2:18]1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 70161234HCID 70161234, compound

Product 1

HCID 54095865HCID 54095865, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the above Wang-Resin methansulfonyl ester and 5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(9H-fluoren-9-ylmethoxy-carbonylamino)-4,7-dihydro-5H-thieno[2,3]pyran-3-carboxylic acid (4.85 g, 8.4 mmol) was added N-methylpyrrolidinone (45 ml). Cesium carbonate (2.2 g, 6.7 mmol) was added and the reaction stirred under nitrogen for 16 h and then at 80° C. for 36 h. The mixture was cooled to room temperature, the resin filtered off, washed with water, methanol, and dichloromethane repeatedly and dried in vacuo for 2 h affording 5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(9H-fluoren-9-ylmethoxy-carbonylamino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid Wang-Resin ester.

Workup

  1. waitat 80° C. for 36 h
  2. filtrationthe resin filtered off
  3. washwashed with water, methanol, and dichloromethane repeatedly
  4. customdried in vacuo for 2 h

Sources & evidence

ORD record
ord-fafa5c3e632a4a468f8242ec10a8f604
Source dataset
uspto-grants-2002_06
Patent number
US06410586B1

Reaction notes

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