Formic Acid → HCID 12992513, compound
Reaction equation
C(O)=[O:2].[C:4](OC(=O)C)(=[O:6])C.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]2[C:19]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:24][CH:23]=3)=[O:21])=[C:18]([C:37]3[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=3)[S:17][C:16]=2[CH:44]=1.C(OC(=O)C)=O>C1COCC1>[NH4+:11].[OH-:2].[OH:43][C:40]1[CH:39]=[CH:38][C:37]([C:18]2[S:17][C:16]3[CH:44]=[C:12]([NH:11][CH:4]=[O:6])[CH:13]=[CH:14][C:15]=3[C:19]=2[C:20](=[O:21])[C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:26][CH:27]=2)=[CH:42][CH:41]=1Participants
7
Procedure
Formic acid (0.18 mL, 4.57 mmol) was added dropwise to a flask containing acetic anhydride (0.36 mL, 3.84 mmol) at 0° C. The mixture was then heated for 2 hrs. at 50° C. At this time the mixture was cooled to room temperature and 0.29 mL of THF was added. In a separate flask the product from Step 1, Example 13 (150 mg, 3.17 mmol) was suspended in 1.2 mL of THF and cooled to −20° C. To this suspension was added the acetic formic anhydride solution (0.088 mL). The reaction was stirred for 2 hrs. then was concentrated to dryness and pumped dry under high vacuum. The crude product was chromatographed in silica gel using 7% MeOH:0.5% NH4OH:methylene chloride as the eluant to obtain 65 mg of the title compound.
Workup
- temperatureThe mixture was then heated for 2 hrs
- customat 50° C
- temperaturecooled to −20° C
- concentrationthen was concentrated to dryness
- custompumped dry under high vacuum
- customThe crude product was chromatographed in silica gel using 7% MeOH
Sources & evidence
- ORD record
- ord-c2b8372c9b2147f1af838d4ed83df7df
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756388B1
Reaction notes
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