Hydrochloric Acid → HCID 57956071, compound

HRID 561896Notes

Reaction equation

HRID 561896 reaction equation
[Cl:1][C:2]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])=[CH:44][C:3]=1[CH2:4][N:5]([CH:41]1[CH2:43][CH2:42]1)[C:6](=[O:40])[CH:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]2[C:33]([Cl:34])=[CH:32][C:31]([CH2:35][CH2:36][CH2:37][OH:38])=[CH:30][C:29]=2[Cl:39])=[CH:20][CH:19]=1)[CH2:8][NH:9]C(=O)OC(C)(C)C.Cl>C(Cl)Cl>[NH2:9][CH2:8][CH:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]2[C:29]([Cl:39])=[CH:30][C:31]([CH2:35][CH2:36][CH2:37][OH:38])=[CH:32][C:33]=2[Cl:34])=[CH:20][CH:19]=1)[C:6]([N:5]([CH2:4][C:3]1[CH:44]=[C:45]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[CH:46]=[CH:47][C:2]=1[Cl:1])[CH:41]1[CH2:42][CH2:43]1)=[O:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86635950HCID 86635950, compound

Product 1

HCID 57956071HCID 57956071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.1 M) of tert-butyl [3-[[2-chloro-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]-2-(4-{2-[2,6-dichloro-4-(3-hydroxypropyl)phenoxy]ethoxy}benzyl}-3-oxopropyl]carbamate from the previous step (1 eq.) was added HCl (4.0 M dioxane solution, 35 eq.). The resulting solution was stirred at RT for 4 h. The reaction was quenched with 2.0 M NH3 in MeOH and concentrated in vacuo. The resulting residue was directly loaded onto a SiO2 column packed with 90:9:1 (v/v) CH2Cl2:MeOH:conc. NH4OH. Elution with the same solvent system furnished the title compound. MS (ESI+): 677.2.

Workup

  1. customThe reaction was quenched with 2.0 M NH3 in MeOH
  2. concentrationconcentrated in vacuo
  3. washElution with the same solvent system

Sources & evidence

ORD record
ord-2e03476a91e04449ad2086e0b3aee3f5
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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