Hydrochloric Acid → HCID 10237534, compound

HRID 2306877Notes

Reaction equation

HRID 2306877 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][S:12][C:13]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=2[NH2:15])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=[O:24].C(O)C(N)(CO)CO.Cl>C(N(C(C)C)CC)(C)C.CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[C:3]([CH2:11][S:12][C:13]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=2[NH:15][C:23](=[O:24])[C:22]([CH3:27])([CH3:26])[CH3:21])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6503Tris(hydroxymethyl)aminomethaneHCID 62493Pivaloyl chlorideHCID 22629949HCID 22629949, compound

Product 1

HCID 10237534HCID 10237534, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

The material from step 2 was suspended in a mixture of diisopropyl ethyl amine (0.15 mL), PS-DMAP resin (50 mg), 2,2-dimethylpropanoyl chloride (0.1 mL) and dichloromethane (7 mL). The reaction was agitated overnight and then treated with PS-Trisamine resin and agitated a further 24 h. The reaction was applied to an Extrelut QE column prepped with 1N HCl, the organic was collected and evaporated under a stream of nitrogen. The residue was chromatographed on silica to afford the title product. MS (ESI+) for C20H22ClNO3S m/z 392 (M+H)+.

Workup

  1. stirringagitated a further 24 h
  2. customthe organic was collected
  3. customevaporated under a stream of nitrogen
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-1eb0546ea153421b9fc5af3b4d2321dd
Source dataset
uspto-grants-2004_12
Patent number
US06828446B2

Reaction notes

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