Pantothenic Acid → [2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-[3-((R)-2,4-dihydroxy-3,3-dimethyl-butyrylamino)-propionylamino]-ethyl ester

HRID 514973

Reaction equation

HRID 514973 reaction equation
[OH:1][C@H:2]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[C:3]([NH:5][CH2:6][CH2:7][C:8]([OH:10])=O)=[O:4].C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH2:45][CH2:46][CH2:47][O:48][C:49](=[O:66])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][C:58]1[C:63]([Cl:64])=[CH:62][CH:61]=[CH:60][C:59]=1[Cl:65]>CN(C=O)C.O>[OH:1][C@H:2]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[C:3]([NH:5][CH2:6][CH2:7][C:8]([NH:45][CH2:46][CH2:47][O:48][C:49](=[O:66])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][C:58]1[C:63]([Cl:64])=[CH:62][CH:61]=[CH:60][C:59]=1[Cl:65])=[O:10])=[O:4]

Participants

8

Reactant 5

HCID 6613Pantothenic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 769604762-(2-(2-((2,6-Dichlorophenyl)amino)phenyl)acetyloxy)ethanamine

Product 1

HCID 91827687[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-[3-((R)-2,4-dihydroxy-3,3-dimethyl-butyrylamino)-propionylamino]-ethyl esterYield 26.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-((R)-2,4-Dihydroxy-3,3-dimethyl-butyrylamino)-propionic acid 6 (0.2 g, 0.0007 mol, 1 eq) in DMF (4 mL) was added triethyl amine (0.31 g, 0.003 mol), EDC.HCl (0.22 g, 0.001 mol), HOBt (0.15 g, 0.001 mol) and [2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-amino-ethyl ester 5 (0.26 g, 0.0007 mol, 1 eq) at rt. The resulting mixture was stirred at room temperature for 16 h. Reaction was monitored by TLC. After completion, reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). Combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure and purified by silica gel column chromatography using Methanol and DCM (3:97) to get 0.11 g (26.4% Yield) of CLX-SYN-G18-C01 as an off white solid; Mass: 539.9 [M+H].

Workup

  1. customReaction
  2. customAfter completion, reaction mixture
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. custompurified by silica gel column chromatography
  7. customto get 0.11 g (26.4% Yield) of CLX-SYN-G18-C01 as an off white solid

Sources & evidence

ORD record
ord-70afac8a5695494f86c31496194e923c
Source dataset
uspto-grants-2015_08
Patent number
US09108942B1

Linked notes

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