Formic Acid → HCID 86751028, compound

HRID 263672Notes

Reaction equation

HRID 263672 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][C@H:13]([C:39]1[CH:44]=[CH:43][C:42]2[O:45][CH2:46][O:47][C:41]=2[CH:40]=1)[C@H:14]([N:16]([CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=1)[C:17]([C@@H:19]1[C@@H:23]([C:24]([OH:26])=[O:25])[CH2:22][C:21](=[O:27])[O:20]1)=[O:18])[CH3:15].C(O)=O.[CH2:51](O)[CH3:52].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][C@H:13]([C:39]1[CH:44]=[CH:43][C:42]2[O:45][CH2:46][O:47][C:41]=2[CH:40]=1)[C@H:14]([N:16]([CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=1)[C:17]([C@@H:19]1[C@@H:23]([C:24]([O:26][CH2:51][CH3:52])=[O:25])[CH2:22][C:21](=[O:27])[O:20]1)=[O:18])[CH3:15]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22874448HCID 22874448, compound

Product 1

HCID 86751028HCID 86751028, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

155 mg of (2S,3S)-2-[N-{(1R,2R,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-5-oxotetrahydrofuran-3-carboxylic acid prepared by deprotecting the ester of the compound of Example 67(1) with formic acid, 13.5 mg of ethanol and 36.0 mg of 4-dimethylaminopyridine, were dissolved in 2 ml of chloroform, and 57.0 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added thereto, followed by stirring at room temperature overnight. The reaction solution was poured into water and extracted with chloroform. The extract solution was dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 123 mg (yield: 76%) of the above-identified compound as slightly yellow oily substance.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-14e0a8da767644f09da120af20639b43
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

Loading…