Pyridine → HCID 67039231, compound

HRID 604585Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]([CH2:13][CH2:14][CH2:15][C:16]([NH:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[O:17])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[N:3]=1.N1C=CC=CC=1.[CH3:41][C:42]([CH3:47])([CH3:46])[C:43](Cl)=[O:44]>>[O:21]([CH2:20][CH2:19][NH:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][C:5]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]([C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[N:3]=[C:2]([NH:1][C:43](=[O:44])[C:42]([CH3:47])([CH3:46])[CH3:41])[S:6]1)[Si:22]([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:24])[CH3:23]

Participants

Reactant 3

HCID 1049Pyridine

HCID 62493Pivaloyl chloride

HCID 67039554HCID 67039554, compound

Product 1

HCID 67039231HCID 67039231, compoundYield 85.2%

Procedure

In the same manner as that in Step 3 of Reference Example 20, from the optically active 4-[5-amino-3-(2,2-dimethylpropionyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl]-N-[2-(tert-butyldimethylsiloxy)ethyl]butanamide (0.0683 g, 0.135 mmol) obtained in Step 6 mentioned above, pyridine (131 μL, 1.62 mmol) and trimethylacetyl chloride (0.166 mL, 1.35 mmol), optically active N-[2-(tert-butyl-dimethylsiloxy)ethyl]-4-[3-(2,2-dimethylpropionyl)-5-(2,2-dimethylpropionylamino)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl]butanamide (68.0 mg, 83%) was obtained.

Sources & evidence

ORD record: ord-23cb8a673f0c4ce0a1486f3300972ca4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910611B2

Reaction notes

Loading…