Hydrochloric Acid → HCID 118120001, compound

HRID 930977Notes

Reaction equation

HRID 930977 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:33]C(=O)OC(C)(C)C)[C:5](=[O:32])[NH:6][CH2:7][CH:8]1[CH2:13][CH2:12][C:11]2[C:14]3[C:19]([NH:20][C:21]4[CH:30]=[CH:29][C:24]5[NH:25][C:26](=[O:28])[S:27][C:23]=5[CH:22]=4)=[N:18][CH:17]=[N:16][C:15]=3[S:31][C:10]=2[CH2:9]1.O1CCOCC1.Cl>C(N(CC)CC)C>[O:28]=[C:26]1[NH:25][C:24]2[CH:29]=[CH:30][C:21]([NH:20][C:19]3[C:14]4[C:11]5[CH2:12][CH2:13][CH:8]([CH2:7][NH:6][C:5](=[O:32])[C@H:4]([CH2:3][CH2:2][OH:1])[NH2:33])[CH2:9][C:10]=5[S:31][C:15]=4[N:16]=[CH:17][N:18]=3)=[CH:22][C:23]=2[S:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131735152HCID 131735152, compound

Product 1

HCID 118120001HCID 118120001, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture comprising 32.5 mg (56 μmol) tert-butyl {(2R)-4-hydroxy-1-oxo-1-[({(7RS)-4-[(2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-7-yl}methyl)amino]butan-2-yl}carbamate (prepared according to example 27), 1.0 mL 1,4-dioxane and 42.7 μL hydrochloric acid (4M in 1,4-dioxane) was stirred at 23° C. overnight. 1 mL N,N-diethylethanamine was added, the solvents removed and the residue purified by chromatography to give 6.3 mg (22%) of the title compound.

Workup

  1. customthe solvents removed
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-9207d62e5dda4de7abf83ca829e38a88
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

Loading…