1-Hydroxybenzotriazole → HCID 86714409, compound

HRID 1750196Notes

Reaction equation

HRID 1750196 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH2:4][CH3:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[C:39]([O:43][C:44](=[O:51])[C@H:45]([CH2:47][CH:48]([CH3:50])[CH3:49])[NH2:46])([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C.C(Cl)CCl>[C:39]([O:43][C:44](=[O:51])[C@@H:45]([NH:46][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:7]([NH:6][CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])=[C:8]([N+:16]([O-:18])=[O:17])[CH:9]=1)[CH2:47][CH:48]([CH3:49])[CH3:50])([CH3:41])([CH3:40])[CH3:42]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 115143484-[(1-Ethylpropyl)amino]-3-nitrobenzoic acidHCID 12451443tert-butyl (2S)-2-amino-4-methylpentanoate hydrochloride

Product 1

HCID 86714409HCID 86714409, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.80 g of 4-(1-ethyl-propylamino)-3-nitro-benzoic acid in 210 ml of dry DMF 1.82 g of HOBT, 7.23 g of EDC and 6.6 ml of DIPEA were added at 0° C. After 30 min 7.24 g of L-leucin-tert.-butylester-hydrochloride and 4.7 ml of DIPEA were added and the reaction was stirred at rt for 4 h. The reaction was then concentrated to about a fifth of its volume and poured into water. It was then extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium carbonate solution and brine, dried over magnesium sulphate and concentrated to yield 11.50 g (100%) of (S)-2-[4-(1-ethyl-propylamino)-3-nitro-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester.

Workup

  1. concentrationThe reaction was then concentrated to about a fifth of its volume
  2. additionpoured into water
  3. extractionIt was then extracted with ethyl acetate three times
  4. washThe combined organic phases were washed with saturated aqueous sodium carbonate solution and brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-97277e8536144bbc81652ed0eafd645d
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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