1,4-Dioxane hydrochloride → HCID 44453366, compound

HRID 133568Notes

Reaction equation

HRID 133568 reaction equation
O1CCOCC1.Cl.[NH2:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][C:45]=1[OH:46])[CH2:12][N:13]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:42])[CH2:20][NH:21][C:22](=[O:41])[C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=2[NH:33]C(OC(C)(C)C)=O)[CH2:14]1>>[NH2:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][C:45]=1[OH:46])[CH2:12][N:13]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:42])[CH2:20][NH:21][C:22](=[O:41])[C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:26]=[CH:25][C:24]=2[NH2:33])[CH2:14]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69213603HCID 69213603, compound

Product 1

HCID 44453366HCID 44453366, compound

Procedure

A 4 M HCl dioxane (2.0 mL) solution of (R)-1-(3-amino-4-hydroxybenzyl)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (20 mg) synthesized according to the method of Example 808 was stirred at room temperature overnight. The solution was concentrated, and the residue was then dissolved in methanol, loaded onto a VarianM SCX column, washed with methanol, subsequently eluted with a 2 M methanol solution of NH3, concentrated and then purified by preparative TLC (SiO2, ethyl acetate/methanol=4:1) to thereby provide (R)-1-(3-amino-4-hydroxybenzyl)-3-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (Compd. No. 2187) (9.6 mg, 59%). The purity was determined by RPLC/MS (86%). ESI/MS m/e 452.3 (M++H, C21H24F3N5O3).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was then dissolved in methanol
  3. washwashed with methanol
  4. washsubsequently eluted with a 2 M methanol solution of NH3
  5. concentrationconcentrated
  6. custompurified by preparative TLC (SiO2, ethyl acetate/methanol=4:1) to thereby provide (R)-1-(3-amino-4-hydroxybenzyl)-3-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (Compd. No

Sources & evidence

ORD record
ord-0070ba61adf14e18ab64dcefb51deb31
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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