Acetic acid, azido-, ethyl ester → Methyl alpha-azido-4-[bis(tert-butoxy)phosphorylhydroxymethyl]cinnamate

HRID 258166Notes

Reaction equation

[N:1]([CH2:4][C:5]([O:7][CH2:8]C)=[O:6])=[N+:2]=[N-:3].[C:10]([O:14][P:15]([CH:22]([OH:31])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:13])([CH3:12])[CH3:11].C[O-].[Na+].[Cl-].[Na+].O.CCOC(C)=O>CO>[N:1]([C:4](=[CH:27][C:26]1[CH:25]=[CH:24][C:23]([CH:22]([P:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O:14][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:16])[OH:31])=[CH:30][CH:29]=1)[C:5]([O:7][CH3:8])=[O:6])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 6.45 g (50 mmol) of ethyl α-azidoacetate and 1.64 g (5.0 mmol) of 4-[bis(tert-butoxy) -phosphorylhydroxymethyl)benzaldehyde 6 in MeOH (20 mL) at -78° C. was added a total of 7.4 mL (40 mmol) of NaOMe, 5.4M in MeOH, dropwise over 5 minutes. The mixture was stirred 5 minutes at -78° C. then an additional 1 hour at 0° C. The resulting light yellow suspension was subjected to an extractive work up (brine/EtOAc) to yield a light yellow crystalline solid, which was triturated with CHCl3 /pet. ether (35°-60° C.) to yield 7 as light yellow crystals, 1.26 g (57%), mp 111°-113° C.

Workup

customan additional 1 hour
customat 0° C
customto yield a light yellow crystalline solid, which
customwas triturated with CHCl3 /pet. ether (35°-60° C.)

Sources & evidence

ORD record: ord-4a22e42a6b104e72b02fc377584c65da
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264607

Reaction notes

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