Sodium Hydroxide → HCID 54670532, compound

HRID 1426946Notes

Reaction equation

HRID 1426946 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]1=[C:25]3[N:26]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1.C([O:30][CH2:31][C:32](Cl)=[O:33])(=O)C.CCN(C(C)C)C(C)C.[OH-].[Na+]>[Cl-].[Na+].O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][N:18]([C:31](=[O:30])[CH2:32][OH:33])[CH2:17][C:16]1=[C:25]3[N:26]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 26297Acetoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 70168839HCID 70168839, compound

Product 1

HCID 54670532HCID 54670532, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a DCM (0.5 mL) solution of (6R)-9-fluoro-13-oxa-2,16,20,21,24-pentaazapentacyclo-[16.5.2.02,6.07,12.021,25]pentacosa-1(24),7,9,11,18(25),19,22-heptaene (Example 21, 6 mg, 0.017 mmol) was added 2-chloro-2-oxoethyl acetate (3.5 mg, 0.025 mmol), followed by DIEA (8.9 μL, 0.051 mmol). The reaction was stirred at ambient temperature overnight, then concentrated, and MeOH (0.2 mL) was added followed by sodium hydroxide (6.8 mg, 0.085 mmol). After stirring at ambient temperature for 5 hours, the reaction was diluted with brine and extracted with several portions of DCM in a phase separator tube. The combined organic extracts were concentrated and purified by reverse-phase column chromatography, eluting with 0-70% acetonitrile/H2O, to provide the title product (3.6 mg, 52% yield). MS (apci) m/z=412.5 (M+H).

Workup

  1. concentrationconcentrated
  2. additionMeOH (0.2 mL) was added
  3. stirringAfter stirring at ambient temperature for 5 hours
  4. extractionextracted with several portions of DCM in a phase separator tube
  5. concentrationThe combined organic extracts were concentrated
  6. custompurified by reverse-phase column chromatography
  7. washeluting with 0-70% acetonitrile/H2O

Sources & evidence

ORD record
ord-2cf11ba8d4b5497fae1449c4d7217394
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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