Triethylamine → HCID 66744601, compound

HRID 1959458Notes

Reaction equation

HRID 1959458 reaction equation
[NH2:1][CH:2]1[C@@H:6]2[CH2:7][N:8]([C:10]3[N:15]=[C:14]([C:16]4[O:20][C:19]([C:21]5[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:23][CH:22]=5)=[N:18][N:17]=4)[C:13]([N:37]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[N:12][CH:11]=3)[CH2:9][C@@H:5]2[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH2:59]([S:61](Cl)(=[O:63])=[O:62])[CH3:60]>C(Cl)Cl>[CH2:59]([S:61]([NH:1][CH:2]1[C@@H:6]2[CH2:7][N:8]([C:10]3[N:15]=[C:14]([C:16]4[O:20][C:19]([C:21]5[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:23][CH:22]=5)=[N:18][N:17]=4)[C:13]([N:37]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[N:12][CH:11]=3)[CH2:9][C@@H:5]2[CH2:4][CH2:3]1)(=[O:63])=[O:62])[CH3:60]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 66744634HCID 66744634, compound

Product 1

HCID 66744601HCID 66744601, compoundYield 650%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[[4-[5-[6-[(3aR,6aS)-6-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-[bis(tert-butoxycarbonyl)amino]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (150 mg, 0.22 mmol) and triethylamine (24 mg, 33 μL, 0.23 mmol) in DCM (1 mL) at 0° C. was added ethanesulfonyl chloride (29 mg, 21 μL, 0.22 mmol). The reaction mixture was stirred for 30 min. The solvent was evaporated and the crude material was purified via silica gel column chromatography using 10 to 70% EtOAc in DCM to obtain tert-butyl N-[[4-[5-[6-[(3aR,6aS)-6-(ethylsulfonylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-[bis(tert-butoxycarbonyl)amino]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (110 mg, 650%). LC/MS m/z 799.5 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-67b572b6a4b5488e94539a2609c94186
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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