Boc-L-Valine → HCID 178449822, compound

HRID 2289998Notes

Reaction equation

HRID 2289998 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:16][C:17]1[CH:42]=[CH:41][C:20]([CH2:21][NH:22][C:23]([C:25]2[CH:26]=[N:27][C:28]3[C:33]([C:34]=2[OH:35])=[CH:32][C:31]([CH2:36][CH2:37][CH2:38]O)=[CH:30][C:29]=3[F:40])=[O:24])=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:4]([O:3][C:1]([NH:8][CH:9]([CH:10]([CH3:11])[CH3:12])[C:13]([O:15][CH2:38][CH2:37][CH2:36][C:31]1[CH:32]=[C:33]2[C:28](=[C:29]([F:40])[CH:30]=1)[N:27]=[CH:26][C:25]([C:23]([NH:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([Cl:16])=[CH:42][CH:41]=1)=[O:24])=[C:34]2[OH:35])=[O:14])=[O:2])([CH3:5])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 83693Boc-L-ValineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178522910HCID 178522910, compound

Product 1

HCID 178449822HCID 178449822, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

N-Boc-valine (0.13 g) is added to a solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from example 110 (0.15 g), EDC hydrochloride (0.11 g), and DMAP (0.016 g) in 4 mL pyridine. The reaction is stirred at room temperature overnight. The solvent is removed in vacuo and the residue partitioned between CH2Cl2 and H2O. The organic layer is washed once with water, and once with brine. The organic layer is then dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow liquid. The residue is adsorbed onto silica and purified by chromatography on a Biotage Flash 40S column (eluent 1% MeOH:CH2Cl2 (1 L) followed by 2% MeOH:CH2Cl2 (2 L)). The product is obtained as a white solid which is further purified by recrystallization with CH2Cl2 /hexanes (0.17 g, 74%).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue partitioned between CH2Cl2 and H2O
  3. washThe organic layer is washed once with water
  4. dry with materialThe organic layer is then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow liquid
  8. custompurified by chromatography on a Biotage Flash 40S column (eluent 1% MeOH:CH2Cl2 (1 L) followed by 2% MeOH:CH2Cl2 (2 L))
  9. customThe product is obtained as a white solid which
  10. customis further purified by recrystallization with CH2Cl2 /hexanes (0.17 g, 74%)

Sources & evidence

ORD record
ord-c41c1487eb1b4a2bb5272b580ee0d8fe
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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