HCID 70373625, compound → HCID 178451070, compound

HRID 652825Notes

Reaction equation

HRID 652825 reaction equation
[NH2:1][C@H:2]1[C@@H:5]([CH2:6][O:7][C:8](=[O:10])[NH2:9])[N:4]([S:11]([OH:14])(=[O:13])=[O:12])[C:3]1=[O:15].[Na:16].S1C2C=CC=CC=2N=C1S[O:27][C:28](=O)/[C:29](/[C:42]1[N:43]=[C:44]([NH2:47])[S:45][CH:46]=1)=[N:30]\[O:31][C:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([CH3:34])[CH3:33]>CC(C)=O.O>[NH2:47][C:44]1[S:45][CH:46]=[C:42](/[C:29](=[N:30]/[O:31][C:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([CH3:34])[CH3:33])/[C:28]([NH:1][C@H:2]2[C@@H:5]([CH2:6][O:7][C:8](=[O:10])[NH2:9])[N:4]([S:11]([OH:14])(=[O:12])=[O:13])[C:3]2=[O:15])=[O:27])[N:43]=1.[Na:16]

Participants

4

Reactant 2

HCID 70373625HCID 70373625, compoundHCID 88278475HCID 88278475, compound

Product 1

HCID 178451070HCID 178451070, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

1.62 g of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-oxo-1-azetidine-sulfonic acid-sodium salt in 180 ml of acetone-water (2:1) are stirred with 3.87 g of (Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl-thioester at room temperature for 15 hours. After removal of the acetone in vacuo and the addition of 50 ml of water, crystals are obtained which are washed with water. The mother liquor is evaporated under reduced pressure at 37° C. and chromatographed (MCI Gel, water as eluting agent). After lyophilization (3S,4S)-3-[(2-amino-4-thiazolyl)-2-(Z)-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulfonic acid-sodium salt is obtained.

Workup

  1. customAfter removal of the acetone in vacuo
  2. additionthe addition of 50 ml of water, crystals
  3. customare obtained which
  4. washare washed with water
  5. customThe mother liquor is evaporated under reduced pressure at 37° C.
  6. customchromatographed
  7. wash(MCI Gel, water as eluting agent)

Sources & evidence

ORD record
ord-e4c7ae3f79a94e25a79f240dafccd6d1
Source dataset
uspto-grants-1987_06
Patent number
US04673739

Reaction notes

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