Trifluoroacetic acid → HCID 10791549, compound

HRID 1068078Notes

Reaction equation

HRID 1068078 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[CH2:11][C@H:12]([OH:26])[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].C(OC(=O)[C@@H](NC(OC(C)(C)C)=O)CCCCN(C(OCC1C=CC=CC=1)=O)C[C@@H](O)CCNC(OCC1C=CC=CC=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[CH2:11][C@@H:12]([OH:26])[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 12052TriethylsilaneHCID 10744014HCID 10744014, compoundHCID 10770600HCID 10770600, compound

Product 1

HCID 10791549HCID 10791549, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the method described for the preparation of 17a, 16b (78 mg, 0.12 mmol) was reacted with trifluoroacetic acid (704 mg, 6.20 mmol) and triethylsilane (140 mg, 11.92 mmol) in CH2Cl2 (0.98 mL) to give 17b (37 mg, 62%) as a colorless oil: 1H NMR δ 1.20-2.10 (m, 8H), 3.05-3.70 (m, 7H), 3.82 (m, 1H), 5.05 (s, 2H), 5.10 (s, 2H), 7.20-7.60 (m, 10H); HRMS m/z calcd for C26H36N3O7 502.2553, found 502.2546. [α]23D+3.6° (c 1.00, CH3OH).

Sources & evidence

ORD record
ord-131d7af15ba14c47b771a2223130c206
Source dataset
uspto-grants-2001_06
Patent number
US06248866B1

Reaction notes

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