Propylene Oxide → HCID 131710768, compound

HRID 1707197Notes

Reaction equation

HRID 1707197 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH2:21])[C:19](=[O:22])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2].C1OC1C.[Cl:27][CH:28]([Cl:42])[C:29]([O:31][NH:32][CH:33]([C:37]1[CH:41]=[CH:40][S:39][CH:38]=1)[C:34](Cl)=[O:35])=[O:30]>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH:21][C:34](=[O:35])[C:33](=[N:32][O:31][C:29](=[O:30])[CH:28]([Cl:27])[Cl:42])[C:37]3[CH:41]=[CH:40][S:39][CH:38]=3)[C:19](=[O:22])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 15573427tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 54430823HCID 54430823, compound

Product 1

HCID 131710768HCID 131710768, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To an ice cold solution of t-butyl 3-acetoxymethyl-7β-aminoceph-3-em-4-carboxylate (1.59 g) and propylene oxide (3.5 mls) in ethyl acetate (15 mls) was added with stirring a 1-M solution of 2-dichloroacetoxyamino-2-(thien-3-yl) acetyl chloride (syn-isomer) (5.3 ml.) in ethyl acetate. After 11/2 hrs. at 20° C. the solution was washed with 2N-HCl, saturated sodium bicarbonate solution and brine. The organic layer was dried and evaporated to give t-butyl 3-acetoxymethyl-7β-[2-dichloroacetoxyimino-2-(thien-3-yl)acetamido]ceph-3-em-4-carboxylate (syn-isomer) as a white foam, (2.8 g, 100%), [α]D +47.0° (c 0.9, DMSO), λmax. (ethanol) 253 nm (ε 13,900), νmax. (CHBr3) 3580 (OH), 3410 (NH), 1790 (β-lactam), 1728 (OCOCH3), 1720 (COO But) and 1700 and 1520 cm.-1 (CONH); τ (CDCl3) values include 2.11 to 2.7 (m; thienyl protons), 7.92 (s; OCOCH3), 8.48 (s; But).

Workup

  1. custom2 hrs
  2. washat 20° C. the solution was washed with 2N-HCl, saturated sodium bicarbonate solution and brine
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-45ff319e0fb74d93b1d85db90e7a1328
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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