Pivaloyl chloride → HCID 67995076, compound

HRID 2042957Notes

Reaction equation

HRID 2042957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)=[CH:23][N:24]=1.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:30]([O:18][CH2:17][C@@H:10]1[C@@H:11]([OH:16])[C@H:12]([OH:15])[C@@H:13]([OH:14])[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:29]=[CH:28][S:27][CH:26]=4)=[CH:23][N:24]=3)[CH:4]=2)[O:9]1)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 51346777HCID 51346777, compound

Product 1

HCID 67995076HCID 67995076, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 48 (150 mg, 0.33 mmol) and DMAP (4 mg, 0.033 mmol) in pyridine (1.0 ml) was added pivaloyl chloride (57 μl, 0.46 mmol) as dropwise at room temperature and stirred for 10 h. The crude product was purified by prep HPLC (C18) to provide the titled compound (83 mg, 47%).

Workup

  1. customThe crude product was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-1a255daf9a7841d28d9c6fce78d784c6
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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