Water → HCID 21517608, compound

HRID 1578901Notes

Reaction equation

HRID 1578901 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[CH:24]([S:25][CH2:26][C:27]#[C:28][CH2:29][O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[NH:23][C:22]2=[O:37])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([C:42](=[O:46])[C:43]([O-:45])=[O:44])(C)(C)C.O>C1C=CC=CC=1>[OH:46][CH:42]([N:23]1[CH:24]([S:25][CH2:26][C:27]#[C:28][CH2:29][O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH:21]([NH:20][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:22]1=[O:37])[C:43]([O:45][C:1]([CH3:7])([CH3:6])[CH3:2])=[O:44]

Participants

5

Reactant 3

HCID 962WaterHCID 21320258HCID 21320258, compoundHCID 54357292HCID 54357292, compound

Product 1

HCID 21517608HCID 21517608, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(Triphenylmethylamino)-4-(4-tetrahydropyranyloxybut-2-ynylthio)azetidin-2-one (934 mg) and t-butylglyoxylate (2.5 g) were refluxed in benzene (20 ml) with provision for the removal of water. After 1 hour the cooled solution was washed with water (6 × 5 ml), dried and evaporated. Chromatography on silica gave 1-(1-hydroxy-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(4-tetrahydropyranyloxybut-2-ynylthio)azetidine-2-one which still contained some t-butylglyoxylate. Re-chromatography on silica affored the pure material as an amorphous solid (519 mg) νmax (CHCl3) 3500, 3350, 1770, 1738 cm-1.

Workup

  1. washAfter 1 hour the cooled solution was washed with water (6 × 5 ml)
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-c06af10d30f6460fa6fce10325d4d7ae
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

Loading…