Hydrochloric Acid → HCID 46174559, compound

HRID 2035594Notes

Reaction equation

HRID 2035594 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[C@H:23]([CH2:34][O:35][CH3:36])[CH2:22]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl>C(Cl)(Cl)Cl>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][NH:24][C@H:23]([CH2:34][O:35][CH3:36])[CH2:22]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67234507HCID 67234507, compound

Product 1

HCID 46174559HCID 46174559, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The product from Step B (0.070 g, 0.14 mmol) was dissolved in CHCl3 (1.4 mL). Then HCl (1.4 mL, 5.7 mmol, 4.0M in dioxane) was added and the mixture stirred at ambient temperature for 5.0 hours. The mixture was filtered directly and the solid washed with CH2Cl2 followed by Et2O and dried. The crude solid was purified by preparative TLC (1 mm, 8% MeOH/DCM with 1% NH3). This provided 0.031 g (56%) of the product as a pale orange solid. MS ESI (+) m/z 390.2 (M+1) detected.

Workup

  1. filtrationThe mixture was filtered directly
  2. washthe solid washed with CH2Cl2
  3. customdried
  4. customThe crude solid was purified by preparative TLC (1 mm, 8% MeOH/DCM with 1% NH3)

Sources & evidence

ORD record
ord-e88eb88df72f410daf518aee1df29aa3
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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