Hydrochloric Acid → HCID 86345074, compound

HRID 1503919Notes

Reaction equation

HRID 1503919 reaction equation
[C:1]([C@H:4]([OH:34])[CH2:5][C@H:6]1[CH2:17][CH2:16][C:15]2[S:14][C:13]3[N:12]=[CH:11][N:10]=[C:9]([O:18][CH:19]4[CH2:24][CH2:23][CH:22]([N:25](C)[C:26](=O)OC(C)(C)C)[CH2:21][CH2:20]4)[C:8]=3[C:7]1=2)(=[O:3])[NH2:2].Cl>ClCCl>[OH:34][C@H:4]([CH2:5][C@H:6]1[CH2:17][CH2:16][C:15]2[S:14][C:13]3[N:12]=[CH:11][N:10]=[C:9]([O:18][CH:19]4[CH2:20][CH2:21][CH:22]([NH:25][CH3:26])[CH2:23][CH2:24]4)[C:8]=3[C:7]1=2)[C:1]([NH2:2])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118567409HCID 118567409, compound

Product 1

HCID 86345074HCID 86345074, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 10-mL round-bottom flask was placed a solution of tert-butyl N-(4-[[(3R)-3-[(2R)-2-carbamoyl-2-hydroxyethyl]-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (0.7 g, 1.16 mmol, 1.00 equiv) in dichloromethane (10 mL) at 0° C. under nitrogen. Then hydrochloric acid (12 M, 2.0 mL) was added and the resulting solution was stirred for 5 h at 0° C. After completion of the reaction, the solvents were evaporated under reduced pressure. The residue was neutralized with 2 M aqueous sodium bicarbonate and extracted with 3×60 mL of dichloromethane. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 400 mg (crude) of (2R)-2-hydroxy-3-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propanamide as a yellow oil. 1H NMR (300 MHz, CD3OD): δ 8.46 (s, 1H), 5.30 (m, 1H), 4.08 (m, 1H), 3.66 (m, 1H), 3.19-3.12 (m, 1H), 3.02-2.96 (m, 1H), 2.74-2.25 (m, 9H), 2.13-2.10 (m, 2H), 1.82-1.68 (m, 3H), 1.45-1.25 (m, 2H). MS: m/z 391 (M+H)+.

Workup

  1. customInto a 10-mL round-bottom flask was placed
  2. customat 0° C.
  3. customAfter completion of the reaction
  4. customthe solvents were evaporated under reduced pressure
  5. extractionextracted with 3×60 mL of dichloromethane
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b3c09d2b485e4279a35a347ca2121627
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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