tert-Butyldiphenylchlorosilane → HCID 86737864, compound

HRID 1277712Notes

Reaction equation

HRID 1277712 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:18])[C@@H:12]2[C@@H:15]([OH:17])[CH3:16])[C:9]=1[C:19]([O-:21])=[O:20])(=[O:3])[CH3:2].[Na+].[C:23]([Si:27](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])([CH3:25])[CH3:24]>O1CCCC1.C1OCCOCCOCCOCCOC1>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:18])[C@@H:12]2[C@@H:15]([OH:17])[CH3:16])[C:9]=1[C:19]([O:21][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 86737865HCID 86737865, compound

Product 1

HCID 86737864HCID 86737864, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sodium (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e64) (50 mg, 50% pure material) in dry tetrahydrofuran (THF) (5 ml) containing 15-crown-5 crown ether (2 drops) and 3 A molecular sieves was treated with tert-butylchlorodiphenylsilane (80 mg). After stirring at r.t. for 20 hr., the THF was evaporated in vacuo and the mixture loaded onto a silica gel column (10 g) and the column eluted with chloroform (10 ml) followed by a chloroform/ethanol mixture (4:1). The fractions containing the ester were combined and evaporated to give tert-Butyldiphenylsilyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e65) as an oil (20 mg), νmax (CH2Cl2) 1785, 1700, 1685, 1625 cm-1. δ(CDCl3) 1.13 (9H,s,C(CH3)3), 1.27 (3H,d,J 6 Hz, CH3CH), 1.77 (3H,s,CH3CO), 2.7-3.2 (2H,m, 4--CH2), 3.22 (1H, m, sharpens to dd on D2O exchange, J1 approx. 5 Hz, J2 approx. 3 Hz, 6--CH), 3.6 (1H, broad, exchanges D2O, OH), 3.9-4.3 (2H,m, 5--CH, 8--CH), 5.60 (1H,d,J 14 Hz, S CH=), 7.02 (1H,dd,J1 14 Hz, J2 10 Hz,d,J 14 Hz on D2O exchange, CH=CH NH), 7.3-7.8 (10H, Ar--H), 8.34 (1H, broad d, exchange D2O, NH) p.p.m. The UV spectrum showed a maximum at about 328 nm.

Workup

  1. custom, the THF was evaporated in vacuo
  2. washthe column eluted with chloroform (10 ml)
  3. additionThe fractions containing the ester
  4. customevaporated

Sources & evidence

ORD record
ord-7e7d27cbc09d4333a770a9d99b29447b
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

Loading…