Sodium Azide → HCID 14842618, compound

HRID 893053Notes

Reaction equation

HRID 893053 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C@@H:5]1[CH2:9][C@H:8](Cl)[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[C@@H:5]1[CH2:9][C@@H:8]([N:19]=[N+:20]=[N-:21])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14842606HCID 14842606, compound

Product 1

HCID 14842618HCID 14842618, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The chloro ester 4a (5.5 g, 19.8 mmol) and NaN3 (5.5 g, 84.6 mmol) were dissolved 200 ml of DMF in a 75° C. oil bath and stirred at this temp. for 64 h, then worked up using method B. This gave 4.5 g (80% crude yield)of an oil, which was used directly in the next step. 1H NMR (CDCl3) δ1.28 (t, 3H), 1.41/1.46 (2s, 9H), 2.17 (m, 1H), 2.32 (m, 1H), 3.52 (m, 1H), 3.70 (dd, 1H), 4.18 (m, 3H), 4.34 (m, 1H). FAB MS; MH+ calc. for C12H21N4O4 =235.1563, found 285.1574.

Sources & evidence

ORD record
ord-9118689d87bc4235ac177a4c98d58191
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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