Triethylamine → HCID 56611481, compound

HRID 1788798Notes

Reaction equation

HRID 1788798 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]1[C@@H:16]([C:17]#[N:18])[NH:15][C:14]1=[O:19].C(N(CC)CC)C.Cl.[Cl:28][CH2:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36]([C:38](=[N:42][O:43][C:44]([C:47]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][CH:52]=2)=[O:48])([CH3:46])[CH3:45])[C:39](Cl)=[O:40])[N:37]=1)=[O:31]>O1CCCC1>[Cl:28][CH2:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36]([C:38](=[N:42][O:43][C:44]([C:47]([O:49][CH2:50][C:51]2[CH:52]=[CH:53][C:54]([N+:57]([O-:59])=[O:58])=[CH:55][CH:56]=2)=[O:48])([CH3:45])[CH3:46])[C:39]([NH:12][C@H:13]2[C@@H:16]([C:17]#[N:18])[NH:15][C:14]2=[O:19])=[O:40])[N:37]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13232642HCID 13232642, compoundHCID 73867520HCID 73867520, compound

Product 1

HCID 56611481HCID 56611481, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 12 ml of tetrahydrofuran was dissolved 0.30 g of (3S, 4S)-3-amino-4-cyano-2-azetidinone p-toluenesulfonate. To the solution were added, under ice-cooling, 0.12 g of triethylamine and, subsequently 0.60 g of 2-(2-chloroacetamidothiazol-4-yl)-2-(1-p-nitrobenzyloxycarbonyl-1-methylethoxyimino)acetyl chloride hydrochloride. The mixture was stirred at room temperature for 40 minutes, followed by concentration under reduced pressure. The residue was purified on a silicagel column [ethyl acetate-chloroformmethanol (3:3:1)] to yield 0.27 g of (3S, 4S)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-(1-p-nitrobenzyloxycarbonyl-1-methylethoxyimino)acetamido]-4-cyano-2-azetidinone.

Workup

  1. additionTo the solution were added, under ice-
  2. temperaturecooling
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe residue was purified on a silicagel column [ethyl acetate-chloroformmethanol (3:3:1)]

Sources & evidence

ORD record
ord-188d82f13f314cc0b26d94522c8c649d
Source dataset
uspto-grants-1987_08
Patent number
US04684724

Reaction notes

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