Sodium Hydroxide → HCID 67223917, compound

HRID 1968214Notes

Reaction equation

HRID 1968214 reaction equation
[CH:1]1([NH:6][C:7](=[O:35])[C@H:8]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[N:21](C(OC(C)(C)C)=O)[CH:22]=[C:23]([C:24]([O:26]C)=[O:25])[C:16]=23)[C@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:6][C:7](=[O:35])[C@H:8]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][CH:22]=[C:23]([C:24]([OH:26])=[O:25])[C:16]=23)[C@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58293432HCID 58293432, compound

Product 1

HCID 67223917HCID 67223917, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
53 °C

Procedure

To crude 1-tert-butyl 3-methyl 4-(((2R,3R)-1-(cyclopentylamino)-3-methyl-1-oxopentan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate was added MeOH (1 mL) and aqueous NaOH (12N, 2mL). The reaction mixture was stirred at 53° C. for 16 h and then purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound. [M+H] calc'd for C20H28N4O3, 373; found, 373.7.

Workup

  1. custompurified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%)
  2. customThe fractions were collected
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1e65bf65ebb04858ab973281d4b54f95
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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