Sodium Hydroxide → HCID 118112338, compound

HRID 2171290Notes

Reaction equation

HRID 2171290 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]3[CH2:16][C@H:17]4[C:22](=[O:23])[N:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:20](=[O:29])[N:18]4[CH2:19][C:8]2=3)=[CH:4][CH:3]=1.[OH-].[Na+:33]>O1CCCC1>[Na+:33].[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]3[CH2:16][C@H:17]4[C:22](=[O:23])[N:21]([CH2:24][CH2:25][C:26]([O-:28])=[O:27])[C:20](=[O:29])[N:18]4[CH2:19][C:8]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 91936958HCID 91936958, compound

Product 1

HCID 118112338HCID 118112338, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-(6-(4-fluorobenzyl)-1,3-dioxo-5,6,11,11a-tetrahydro-1H-imidazo[1′,5′:1,6]pyrido[3,4-b]indol-2(3H)-yl)propanoic acid (A) (40.35 g, 95.7 mmol) dissolved in tetrahydrofuran (960 mL) in 2 L round bottom flask equipped with addition funnel was degassed and cooled in ice water bath. 1M NaOH (86.2 mL, 86.2 mmol) was added dropwise over 3 hr at 0° C. The solvent removed under reduce pressure to afford (S)-3-(6-(4-fluorobenzyl)-1,3-dioxo-5,6,11,11a-tetrahydro-1H-imidazo[1′,5′:1,6]pyrido[3,4-b]indol-2(3H)-yl)propanoic acid sodium salt (Compound A sodium salt; 42.4 g, 100%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 7.53 (d, 1H), 7.47 (d, 1H), 7.16-7.02 (m, 6H), 5.40 (q, 2H), 4.89 (d, 1H), 4.36-4.28 (m, 2H), 3.56-3.49 (m, 2H), 3.27-3.20 (m, 1H), 2.76-2.67 (m, 1H), 2.17-2.11 (m, 2H); LC-MS [M+H+ 422].

Workup

  1. customequipped with addition funnel
  2. customwas degassed
  3. temperaturecooled in ice water bath
  4. customThe solvent removed

Sources & evidence

ORD record
ord-1a4482134ae247fcb4af437bde9e6319
Source dataset
uspto-grants-2015_06
Patent number
US09051320B1

Reaction notes

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