Sodium Azide → HCID 131712978, compound

HRID 355223Notes

Reaction equation

HRID 355223 reaction equation
[Si]([N:8]1[C@@H:11]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:10]([CH2:32][OH:33])[C:9]1=[O:34])(C(C)(C)C)(C)C.[N-]=[N+]=[N-].[Na+]>CN(P(N(C)C)(N(C)C)=O)C>[OH:33][CH2:32][C@H:10]1[C@H:11]([S:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:8][C:9]1=[O:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 70530323HCID 70530323, compound

Product 1

HCID 131712978HCID 131712978, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of trans 1-t-Butyldimethylsilyl-3-hydroxymethyl-4-triphenylmethylthio-2-azetidinone (9.3 g, 19 mmol) in HMPA-10% H2O (40 ml) was added sodium azide (1.5 g, 23 mmol) and the mixture stirred at room temperature for 4.5 h, followed by partition between water and a mixture of ether (60 ml) and petroleum ether (40 ml). The organic phase was washed with water several times, dried and concentrated to give an oil which crystallized from CH2Cl2 -ether to give the title compound as a solid, mp 160°-162° C., Hmr (CDCl3) δ: 7.4 (15H, m), 4.48 (1H, d, J=2.3, 4-H), 3.75 (2H, m) and 3.22 ppm (1H, m).

Workup

  1. customby partition between water
  2. additiona mixture of ether (60 ml) and petroleum ether (40 ml)
  3. washThe organic phase was washed with water several times
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil which
  7. customcrystallized from CH2Cl2 -ether

Sources & evidence

ORD record
ord-5557ece8e2ed436f9dbddb868d253d03
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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