Triethylamine → HCID 86735541, compound

HRID 1679186Notes

Reaction equation

HRID 1679186 reaction equation
[CH3:1][S:2][C:3]1[S:4][CH2:5][C:6]([OH:27])([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[N:8]=1.CCN(CC)CC.[N:35]([CH2:38][C:39](Cl)=[O:40])=[N+:36]=[N-:37]>C(Cl)Cl>[N:35]([CH:38]1[C:39](=[O:40])[N:8]2[CH:7]([C:9]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)=[O:10])[C:6]([OH:27])([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH2:5][S:4][C@:3]12[S:2][CH3:1])=[N+:36]=[N-:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109095582-azidoacetyl ChlorideHCID 20364197HCID 20364197, compound

Product 1

HCID 86735541HCID 86735541, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of crude p-nitrobenzyl 2-methylthio-5-hydroxy-5-acetoxymethyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate (6.31 g., 15.23 mMol) in andydrous CH2Cl2 (75 ml.) is cooled to -78° C. under a N2 atmosphere. Et3N (2.97 ml., 21.3 mMol) is added to the stirring solution followed by dropwise addition of a solution of azidoacetyl chloride (1.85 ml., 21.2 mMol) in CH2Cl2 (20 ml.). The resulting solution is allowed to warm slowly to room temperature. The solution is washed with H2O (3x) and brine, dried with MgSO4, filtered, and concentrated in vacuo to a dark, reddish-brown, viscous oil (7.3 g.). This material is purified by chromatography on silica gel (140 g.). Elution of the column with 10% EtOAc/Oh provides p-nitrobenzyl 7-azido-6-methylthio-3-hydroxy-3-acetoxymethyl-cepham-4-carboxylate (4.10 g.) as a dark oil: ir (CHCl3) 2.91, 4.72, 5.58, 5.73, 6.20, 6.55, and 7.39μ; nmr (CDCl3)δ 2.13 (s, 3, COCH3), 2.23 (s, 3, SCH3), 2.83, 3.63 (ABq, 2, J=14Hz, SCH2), 4.17 (s, 1, OH), 4.30, 4.57 (ABq, 2, J=12Hz, CH2OAc), 4.87 (s, 2, H4 and H7), 5.37 (s, 2, CH2Ar), and 7.60, 8.25 (ABq, 4, J=9Hz, ArH); mass spectrum m/e 497 (M+), 469, 454, 422, 414, 368, 354, 341, 311, 299, 278, 261, and 136.

Workup

  1. washThe solution is washed with H2O (3x) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a dark, reddish-brown, viscous oil (7.3 g.)
  5. customThis material is purified by chromatography on silica gel (140 g.)
  6. washElution of the column with 10% EtOAc/Oh

Sources & evidence

ORD record
ord-36de924b70784d7bbf1d601604f479e1
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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