Sodium Azide → HCID 10261539, compound

HRID 843562Notes

Reaction equation

HRID 843562 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].S(O[CH:16]([CH:21]([CH3:24])[CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[N:1]([C@H:16]([C@@H:21]([CH3:24])[CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22610998HCID 22610998, compound

Product 1

HCID 10261539HCID 10261539, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (1.20 g, 18.6 mmol) was added to a stirred solution of methyl 2-tosyloxy-3-methylpentanoate (3.29 g, 10.9 mmol) in DMF (30 mL). The solution was kept at 50° C. for 24 h, then partitioned between EtOAc and water. The aqueous layer was separated and extracted with EtOAc (3×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give a deep yellow oil (1.51 g, 81%), IR (neat) v 3500-3000 (very br m), 2970 (s), 2939 (br m), 2111 (s), 1736 (s), 1472 (w), 1387 (w), 1225 (br m), 1175 (w), 1086 (w), 732 (s) cm−1; 1H NMR (300 MHz, CDCl3) δ 0.93 (t, 3H), 0.97 (d, 3H), 1.22 & 1.43 (m, 1H), 1.96 (m, 1H), 3.78 (s, 3H), 3.85 (d, 2H); CIMS 172.1 (M+H).

Workup

  1. custompartitioned between EtOAc and water
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-beb82b6e903a476ea3597cdc4f977d6a
Source dataset
uspto-grants-2002_04
Patent number
US06380156B1

Reaction notes

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