Water → HCID 131723058, compound

HRID 2271222Notes

Reaction equation

HRID 2271222 reaction equation
[NH2:1][C@H:2]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:3][NH:4][C:5](=[O:41])[CH2:6][NH:7][C:8]([CH:10]([CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1)[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:9].C(N(CC)CC)C.[C:54]1([S:60](Cl)(=[O:62])=[O:61])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.O>ClCCl>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][CH2:11][CH:10]([C:8]([NH:7][CH2:6][C:5]([NH:4][CH2:3][C@H:2]([NH:1][S:60]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)(=[O:62])=[O:61])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:41])=[O:9])[CH2:26][CH2:27][CH:28]2[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:32][CH2:33]2)[CH2:14][CH2:15]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 131723059HCID 131723059, compound2×

Product 1

HCID 131723058HCID 131723058, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-{3-{[(2-{[(2S)-2-amino-3-ethoxy-3-oxopropyl]amino}-2-oxoethyl)amino]carbonyl}-5-[1-(tert-butoxycarbonyl)-4-piperidyl]pentyl}tetrahydro-1(2H)-pyridinecarboxylate (compound 37) (3.31 g, 4.8 mmol) is dissolved in 50 ml of dichloromethane containing triethylamine (1.04 g, 5 mmol) and benzenesulphonyl chloride (0.9 g, 5 mmol) is then added at about 5° C. After 2 hours at room temperature, water is added. The organic phase is washed with 1N HCl and then with water, dried over sodium sulphate and then evaporated to give the crude product, which is purified by flash chromatography (15/1 dichloromethane/methanol) to give 2.8 g of a white solid.

Workup

  1. additionis then added at about 5° C
  2. washThe organic phase is washed with 1N HCl
  3. dry with materialwith water, dried over sodium sulphate
  4. customevaporated
  5. customto give the crude product, which
  6. customis purified by flash chromatography (15/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-3ef6c6f60bed4ea0b178cc0dcc0d9620
Source dataset
uspto-grants-2001_12
Patent number
US06333338B1

Reaction notes

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