Dimethyl Sulfoxide → Boc-Tyr(Bzl)-aldehyde

HRID 263775Notes

Reaction equation

HRID 263775 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([NH:18][C@H:19]([CH2:35][OH:36])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([NH:18][C@H:19]([CH:35]=[O:36])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:26]=1)([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7019534Boc-tyr(bzl)-OL

Product 1

HCID 7015729Boc-Tyr(Bzl)-aldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Analogously to Example 21 B) 1)c), a solution of 3.5 ml of (49 mmol) of DMSO in 60 ml of methylene chloride is added at -60° C. to 4.76 g (37.5 mmol) of oxalyl chloride in 33.6 ml of methylene chloride. The addition of 8.94 g (25 mmol) of N-Boc-(p-benzyloxyphenylalaninol) in 150 ml of methylene chloride, 14 ml (100 mmol) of triethylamine in 30 ml of methylene chloride and aqueous working up (extraction of the aqueous phases with ethyl acetate) yields the crystalline title compound: TLC Rf (A)=0.71; 1H-NMR (200 MHz, CDCl3): 1.44 (s, 9 H), 3.06 (d, J=6 Hz, 2 H), 4.39 (m, 1 H), 6.86-6.98 and 7.03-7.15 (2m, each 2 H), 7.30-7.48 (m, 5 H), 9.62 (s, 1 H).

Workup

  1. extractionextraction of the aqueous phases with ethyl acetate)

Sources & evidence

ORD record
ord-407f2d9488ff4da6be6adc2ff965037c
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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