Triethylamine → HCID 86742708, compound

HRID 2292352Notes

Reaction equation

HRID 2292352 reaction equation
[O:1]=[C:2]1[C@@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][NH:3]1.Cl[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19].C(N(CC)CC)C.[OH:31][C:32]1[CH:33]=[C:34]([CH2:39][C:40]([NH:42][NH2:43])=[O:41])[CH:35]=[CH:36][C:37]=1[OH:38]>C(OCC)(=O)C.ClCCl.CCOCC>[OH:31][C:32]1[CH:33]=[C:34]([CH2:39][C:40]([NH:42][NH:43][S:18]([NH:21][C:22]([N:3]2[CH2:4][C@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:2]2=[O:1])=[O:23])(=[O:20])=[O:19])=[O:41])[CH:35]=[CH:36][C:37]=1[OH:38]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 15706331HCID 15706331, compound

Product 1

HCID 86742708HCID 86742708, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 1.10 g of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (5.0 mmol) in 40 ml of dry ethyl acetate, 0.45 ml (5.0 mmol) of chlorosulfonyl isocyanate was added with stirring. The mixture was stirred for 1 hour at room temperature and then cooled to 0° C. After the dropwise addition of a solution of 2.09 ml (15.0 mmol) of triethylamine in 10 ml of dry dichloromethane and solution A, stirring was continued for 2.5 hours at 0° C. Ice water was added, and the organic layer was separated and washed successively with cold buffer solution (citrate pH 2) and brine. Drying (magnesium sulfate) and evaporation in vacuo gave a residue which solidified by stirring with ether; yield: 2.1 g.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 1 hour at room temperature
  3. stirringstirring
  4. customthe organic layer was separated
  5. washwashed successively with cold buffer solution (citrate pH 2) and brine
  6. customDrying
  7. custom(magnesium sulfate) and evaporation in vacuo
  8. customgave a residue which

Sources & evidence

ORD record
ord-4585be04351c4709915427243d6cc656
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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