Hydrochloric Acid → HCID 86591690, compound

HRID 1295333Notes

Reaction equation

HRID 1295333 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[C:5]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[N:6]=1.[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29]1[O:30][C:31]([CH3:46])=[C:32]([CH2:34][O:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][C:43](O)=[O:44])=[CH:38][CH:37]=2)[N:33]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl>O.CN(C)C=O>[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29]1[O:30][C:31]([CH3:46])=[C:32]([CH2:34][O:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][C:43]([NH:1][C:2]3[S:3][C:4]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:5]([C:7]4[CH:16]=[CH:15][C:14]5[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=5[CH:8]=4)[N:6]=3)=[O:44])=[CH:38][CH:37]=2)[N:33]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22930712HCID 22930712, compoundHCID 69429345HCID 69429345, compound

Product 1

HCID 86591690HCID 86591690, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 3-[2-amino-4-(5,6,7,8-tetrahydro-2-naphthyl)-5-thiazolyl]propionate (270 mg), [4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetic acid (250 mg), WSC (170 mg), HOBt (135 mg) and N,N-dimethylformamide (10 ml) was stirred for 3 days. The reaction mixture was poured into water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was dissolved in ethanol (9 ml)-tetrahydrofuran (1 ml) and 1N aqueous sodium hydroxide solution (2 ml) was added at 0° C. The mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-[2-[[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetylamino]-4-(5,6,7,8-tetrahydro-2-naphthyl)-5-thiazolyl]propionic acid (270 mg,57%) was obtained as an amorphous oil from a fraction eluted with acetone-hexane (3:2, volume ratio).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethanol (9 ml)-tetrahydrofuran (1 ml) and 1N aqueous sodium hydroxide solution (2 ml)
  6. additionwas added at 0° C
  7. stirringThe mixture was stirred at room temperature for 2 hrs
  8. additionThe reaction mixture was poured into water
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with water
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-f365480cc90f47dca4349bf83fee58a5
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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