Sodium Hydroxide → 6-Chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylic Acid

HRID 541941Notes

Reaction equation

HRID 541941 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[C:9]([C:26]([O:28]C)=[O:27])[CH:10]=[C:11]([CH:25]=3)[O:12][CH2:13][CH2:14][S:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][CH:17]=3.[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[C:9]([C:26]([OH:28])=[O:27])[CH:10]=[C:11]([CH:25]=3)[O:12][CH2:13][CH2:14][S:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][CH:17]=3

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57962117Methyl 6-chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylate

Product 1

HCID 579621096-Chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylic AcidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 6-chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylate (450 mg, 1.1 mmol) in methanol (2.3 mL) and tetrahydrofuran (4.5 mL) was treated with 1 M sodium hydroxide (2.1 mL, 2.1 mmol) dropwise and heated at 60° C. for 16 h. The reaction mixture was cooled to 0° C. and quenched with 1 M HCl (3.2 mL). The resultant suspension was diluted with a small amount of water, filtered, and washed with cold acetonitrile to give the desired product (420 mg, 97%) as a white solid. LCMS for C19H16ClN4O3S (M+H)+: m/z=414.9.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with 1 M HCl (3.2 mL)
  3. additionThe resultant suspension was diluted with a small amount of water
  4. filtrationfiltered
  5. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-3d5f045d0fa84db48190006e4f577460
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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