Trifluoroacetic acid → HCID 66546087, compound

HRID 529595Notes

Reaction equation

HRID 529595 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([C@@H:15]([CH2:35][CH2:36][C@@H:37]([C:47](=[O:65])[NH:48][C@H:49]1[CH2:55][CH2:54][S:53][C@H:52]2[CH2:56][CH2:57][CH2:58][C@@H:59]([C:60]([O:62][CH3:63])=[O:61])[N:51]2[C:50]1=[O:64])[CH2:38][CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[C:16]([NH:18][C@H:19]1[CH2:25][CH2:24][S:23][C@H:22]2[CH2:26][CH2:27][CH2:28][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[N:21]2[C:20]1=[O:34])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([C@H:15]([C:16]([NH:18][C@H:19]1[CH2:25][CH2:24][S:23][C@H:22]2[CH2:26][CH2:27][CH2:28][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[N:21]2[C:20]1=[O:34])=[O:17])[CH2:35][CH2:36][C@@H:37]([C:47](=[O:65])[NH:48][C@H:49]1[CH2:55][CH2:54][S:53][C@H:52]2[CH2:56][CH2:57][CH2:58][C@@H:59]([C:60]([O:62][CH3:63])=[O:61])[N:51]2[C:50]1=[O:64])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68311040HCID 68311040, compound

Product 1

HCID 66546087HCID 66546087, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.1 mL) was added to a 0° C. solution of methyl (4S,7S,10aS)-4-(((2R,5R)-2-benzyl-8-tert-butoxy-5-(((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepin-4-yl)carbamoyl)-8-oxooctanoyl)amino)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (45 mg, 0.053 mmol) in DCM (0.2 mL). The reaction mixture was then stirred at rt for 4 hr. The reaction mixture was concentrated and dried under vacuum. The residue was purified by RP prep-HPLC to give (4R,7R)-7-benzyl-8-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-4-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamoyl)-8-oxooctanoic acid (8.5 mg, 0.011 mmol, 20% yield) as a white solid. Anal. Calcd. for C38H52N4O10S2 m/z 788.5. found: 789.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.59 (1H, d, J=5.5 Hz), 7.29-7.10 (6H, m), 5.44-5.29 (2H, m), 5.24-4.96 (6H, m), 3.72 (3H, s), 3.69 (3H, s), 3.30-3.19 (1H, m), 3.18-3.08 (1H, m), 2.97-2.68 (4H, m), 2.50-2.17 (6H, m), 2.10-1.91 (5H, m), 1.90-1.54 (11H, m), 1.53-1.39 (2H, m).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum
  3. customThe residue was purified by RP prep-HPLC

Sources & evidence

ORD record
ord-a3a044d39b454589a615efa2afc8ace4
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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