Dichloromethane → HCID 89644203, compound

HRID 1746840Notes

Reaction equation

HRID 1746840 reaction equation
[CH3:1][N:2]([CH3:57])[C:3]1[S:4][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([C@H:17]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][C:33]=3[O:34][CH3:35])[C:30]([NH:36]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:29][CH:28]=[CH:27]4)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]2=[O:56])(=[O:10])=[O:9])=[CH:6][N:7]=1.[Cl:58]CCl>O1CCOCC1.Cl>[ClH:58].[CH2:21]([O:20][C:18](=[O:19])[C@H:17]([N:14]1[CH2:15][CH2:16][C@H:12]([NH:11][S:8]([C:5]2[S:4][C:3]([N:2]([CH3:1])[CH3:57])=[N:7][CH:6]=2)(=[O:9])=[O:10])[C:13]1=[O:56])[CH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[C:30]([NH2:36])=[N:29][CH:28]=[CH:27]2)[CH3:22]

Participants

5

Reactant 2

HCID 6344Dichloromethane2×HCID 131733550HCID 131733550, compound

Product 1

HCID 89644203HCID 89644203, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The ethyl (2R)-2-[(3S)-3-(2-(dimethylamino)thiazol-5-ylsulphonylamino)-2-oxopyrrolidin-1-yl]-3-(7-methoxy-1-(tritylamino)isoquinolin-6-yl)propanoate obtained above (0.35 g, 0.44 mmol) is dissolved in 5 ml of dichloromethane. The medium is cooled to 0° C. and 0.5 ml of a 4N solution of hydrochloric acid in dioxane is added. The medium is stirred at 20° C. for 18 h. It is concentrated to dryness and the residue is triturated from ether and filtered off. It is purified on a column of silica (40 g, gradient CH2Cl2/MeOH/NH4OH; 100:0 to 90:10:0.5). The product thus obtained is dissolved in 5 ml of dichloromethane and salified with 0.5 ml of a 4N solution of hydrochloric acid in dioxane. The medium is concentrated and the residue is triturated from ether and dried over P2O5. 230 mg of a solid are obtained.

Workup

  1. concentrationIt is concentrated to dryness
  2. customthe residue is triturated from ether
  3. filtrationfiltered off
  4. customIt is purified on a column of silica (40 g, gradient CH2Cl2/MeOH/NH4OH; 100:0 to 90:10:0.5)
  5. customThe product thus obtained
  6. concentrationThe medium is concentrated
  7. customthe residue is triturated from ether
  8. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-1bf722bef72a4c1ead4bf306631403e6
Source dataset
uspto-grants-2015_10
Patent number
US09150544B2

Reaction notes

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