Water → HCID 18330077, compound

HRID 2271225Notes

Reaction equation

HRID 2271225 reaction equation
Cl.[NH2:2][CH:3]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4]([NH:6][CH2:7][CH:8]([NH:14][S:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])=[O:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5].C(N(C(C)C)CC)(C)C.[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][CH:53]([CH2:56][CH2:57][CH:58]([CH2:62][CH2:63][CH:64]2[CH2:69][CH2:68][N:67]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:66][CH2:65]2)[C:59](F)=[O:60])[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44].O>ClCCl>[C:73]([O:72][C:70]([N:67]1[CH2:68][CH2:69][CH:64]([CH2:63][CH2:62][CH:58]([C:59]([NH:2][CH:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:4]([NH:6][CH2:7][CH:8]([NH:14][S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(=[O:17])=[O:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])=[O:60])[CH2:57][CH2:56][CH:53]2[CH2:54][CH2:55][N:50]([C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])[CH2:51][CH2:52]2)[CH2:65][CH2:66]1)=[O:71])([CH3:76])([CH3:75])[CH3:74]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 18330082HCID 18330082, compoundHCID 18330089HCID 18330089, compound

Product 1

HCID 18330077HCID 18330077, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-[(2-amino-2-phenylethanoyl)amino]-2-[(2-naphthylsulphonyl)amino]propanoate hydrochloride (1.7 g, 3 mmol) and diisopropylethylamine (0.8 g, 6.2 mmol) are added, at room temperature, to a solution of 4-[1-(tert-butoxycarbonyl)-4-piperidyl]-2-{2-[1-(tert-butoxycarbonyl)-4-piperidyl]ethyl}butanoyl fluoride (ref. synthesis B-1) (1.55 g, 3 mmol) in 50 ml of dichloromethane. After stirring for 3 hours, water is added. The organic phase is washed with water, dried over sodium sulphate and evaporated to give the crude product, which is purified by flash chromatography (20/1 dichloromethane/methanol) to give 1.2 g of a white solid.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customto give the crude product, which
  5. customis purified by flash chromatography (20/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-3dfd8c873f0c465cad82f9748bc0f6a8
Source dataset
uspto-grants-2001_12
Patent number
US06333338B1

Reaction notes

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