Hydrochloric Acid → HCID 57137594, compound

HRID 1872812Notes

Reaction equation

HRID 1872812 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:36][C:37](OC1C=CC=CC=1)=[O:38])[C:15]([O:17][C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:36][C:37]([NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)=[O:38])[C:15]([O:17][C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 57213565HCID 57213565, compound

Product 1

HCID 57137594HCID 57137594, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3S)-3-[(2S)-5-benzyloxycarbonyl-2-(phenoxycarbonylamino)pentanoyl]oxyhexadecanamide (1.70 g) and 2-aminopyridine (2.56 g) in pyridine (10 ml) was stirred at 70° C. for 64 hours, and then poured into a mixture of ethyl acetate (100 ml) and 1N hydrochloric acid (100 ml). The organic phase was washed with 1N hydrochloric acid (100 ml), 0.5N hydrochloric acid (100 ml), saturated aqueous sodium bicarbonate (100 ml), and brine (50 ml) successively, dried over magnesium sulfate, and evaporated to dryness. The residue was chromatographed on silica gel (300 cc) eluting with a mixture of dichloromethane and acetone (2:1 - 1:1) to give (3S)-3-[(2S)-5-benzyloxycarbonyl-2-{3-(2-pyridyl)ureido}pentanoyl]oxyhexadecanamide (1.14 g).

Workup

  1. washThe organic phase was washed with 1N hydrochloric acid (100 ml), 0.5N hydrochloric acid (100 ml), saturated aqueous sodium bicarbonate (100 ml), and brine (50 ml) successively
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue was chromatographed on silica gel (300 cc)
  5. washeluting with a mixture of dichloromethane and acetone (2:1 - 1:1)

Sources & evidence

ORD record
ord-8ea98ea43609458784b5e277eab00466
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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