Tetrahydrofuran → 3-(6-methoxy-alpha-methyl-2-naphthalenacetyl)-(R)-2-oxothiazolidin-4-carboxylic acid 4-(bromobutyl) ester

HRID 749222Notes

Reaction equation

HRID 749222 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:25])[C:14]([N:16]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19][S:18][C:17]1=[O:24])=[O:15])[CH:7]=[CH:6]2.O1[CH2:30][CH2:29][CH2:28][CH2:27]1.C(Br)(Br)(Br)[Br:32]>>[Br:32][CH2:27][CH2:28][CH2:29][CH2:30][O:22][C:21]([C@@H:20]1[CH2:19][S:18][C:17](=[O:24])[N:16]1[C:14](=[O:15])[CH:13]([CH3:25])[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)=[O:23]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 866029743-(6-methoxy-alpha-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acid

Product 1

HCID 866029753-(6-methoxy-alpha-methyl-2-naphthalenacetyl)-(R)-2-oxothiazolidin-4-carboxylic acid 4-(bromobutyl) esterYield 19.6%

Procedure

To a solution of 3-(6-methoxy-α-methyl-2-naphthalenacetyl)-(R)-2-oxothiazolidin-4-carboxylic acid (6.79 g, 18.9 mmoles) in tetrahydrofuran (100 ml) triphenylphosphine (9.91 g, 37.8 mmoles) and carbon tetrabromide (12.53 g, 37.8 mmoles) are added. The reaction mixture is left under stirring for 16 hours at room temperature, then the solvent is removed by evaporation at reduced pressure. The obtained crude product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3. 1.83 g of the ester are obtained in the form of an oil.

Workup

  1. waitThe reaction mixture is left
  2. customthe solvent is removed by evaporation at reduced pressure
  3. customThe obtained crude product
  4. customis purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3

Sources & evidence

ORD record
ord-50e04c7a7895454c9153e95469e5c788
Source dataset
uspto-grants-2008_07
Patent number
US07402600B2

Reaction notes

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