Trifluoroacetic acid → HCID 10507563, compound

HRID 1068080Notes

Reaction equation

HRID 1068080 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH2:11][C@H:12]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:3]([OH:5])=[O:4].N[C@@H](CCCCN(C(OCC1C=CC=CC=1)=O)C[C@@H](O)CCNC(OCC1C=CC=CC=1)=O)C(O)=O.FC(F)(F)C(O)=O.O1C=CCCC1>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])[CH2:11][C@@H:12]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 80803,4-dihydro-2H-pyranHCID 10791549HCID 10791549, compoundHCID 10841069HCID 10841069, compound

Product 1

HCID 10507563HCID 10507563, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the method described for the preparation of 18a, 17b (37 mg, 73.8 μmol) was reacted with trifluoroacetic acid (17 mg, 0.15 mmol) and 3,4-dihydro-2H-pyran (46 mg, 50 μL, 0.55 mmol) in CH2Cl2 (2 mL) to give 18b (25 mg, 58%) as a colorless oil: 1H NMR δ 1.26-1.96 (m, 14H), 3.02-4.04 (m, 10H), 4.32-4.63 (m, 1H), 5.06 (s, 2H), 5.11 (s br, 2H), 7.22-7.40 (m, 10H); HRMS m/z calcd for C31H44N3O8 586.3128, found 586.3137.

Sources & evidence

ORD record
ord-6f39bd36bb2f4b7bac1704df3a19cd3f
Source dataset
uspto-grants-2001_06
Patent number
US06248866B1

Reaction notes

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