tert-butyl (2S)-2-amino-4-methylpentanoate → HCID 131711840, compound

HRID 1855749Notes

Reaction equation

HRID 1855749 reaction equation
ClC1C(O[C:9](=[O:24])[C@H:10]([CH2:22][OH:23])[NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=C(Cl)C(Cl)=C(Cl)C=1Cl.[NH2:29][C@H:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33]>CN(C=O)C.C1C=CC2N(O)N=NC=2C=1>[CH2:15]([O:14][C:12]([NH:11][C@H:10]([C:9]([NH:29][C@H:30]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:24])[CH2:22][OH:23])=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoateHCID 14802666HCID 14802666, compound

Product 1

HCID 131711840HCID 131711840, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of benzyloxycarbonyl-serine pentachlorophenyl ester (Z-Ser-OPcp, 19.5 g, 40 mmol) in distilled DMF (100 ml) is added at 0°-5° C. to a stirred solution of H-Leu-OBut (7.5 g, 40 mmol) and HOBt (100 mg) in distilled DMF. The solution is kept at 0° C. for two days and then evaporated to dryness under reduced pressure. The residue is subjected to chromatography on silica gel (1300 g) using hexane-ethyl acetate (1:3) as the eluant. The pure fractions are pooled and evaporated to dryness to yield 11.39 g of the title compound; NMR(CDCl3) δ 0.85 (m, 6H), 1.45 (s, 9H), 7.3 (s, 5H); amino acid analysis: Leu (1.00), Ser (0.93).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-4ca456e6f3fc4b18aa7c7b3cd51a617e
Source dataset
uspto-grants-1980_08
Patent number
US04216209

Reaction notes

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