Hydrochloric Acid → 4-[(S)-2-({4-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-4-ethoxycarbonyl-butyryl]-piperazine-1-carboxylic acid ethyl ester

HRID 1185432Notes

Reaction equation

HRID 1185432 reaction equation
Cl.[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:54])[C@@H:14]([NH:24][C:25]([C:27]2[CH:36]=[C:35]([O:37][CH2:38][C:39]([N:41]3[CH2:45][CH2:44][CH2:43][C@H:42]3[C:46](=[O:52])[NH:47][CH:48]3[CH2:51][CH2:50][CH2:49]3)=[O:40])[C:34]3[C:29](=[CH:30][C:31]([CH3:53])=[CH:32][CH:33]=3)[N:28]=2)=[O:26])[CH2:15][CH2:16][C:17]([O:19][C:20](C)(C)[CH3:21])=[O:18])[CH2:9][CH2:8]1)=[O:6])[CH3:3].C1(C)C=CC=CC=1>C(O)C>[CH2:2]([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13](=[O:54])[C@@H:14]([NH:24][C:25]([C:27]2[CH:36]=[C:35]([O:37][CH2:38][C:39]([N:41]3[CH2:45][CH2:44][CH2:43][C@H:42]3[C:46](=[O:52])[NH:47][CH:48]3[CH2:49][CH2:50][CH2:51]3)=[O:40])[C:34]3[C:29](=[CH:30][C:31]([CH3:53])=[CH:32][CH:33]=3)[N:28]=2)=[O:26])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][CH2:12]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 685988634-[(S)-4-tert-Butoxycarbonyl-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 685982564-[(S)-2-({4-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-4-ethoxycarbonyl-butyryl]-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml of a saturated solution of hydrochloric acid in ethanol 5 g of 4-[(S)-4-tert-Butoxycarbonyl-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester was added and the mixture was stirred for 2 h. Then, 30 ml of toluene was added and the solvents were removed under reduced pressure. The residue was filtered through a plug of silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. The residue was purified by re-crystallisation from n-heptane/ethyl acetate and dried under reduced pressure. Yield: 3.8 g MS (ES+): m/e=709.

Workup

  1. customthe solvents were removed under reduced pressure
  2. filtrationThe residue was filtered through a plug of silica gel eluting with a gradient of n-heptane/ethyl acetate
  3. additionThe fractions containing the product
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by re-crystallisation from n-heptane/ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-8f51e6bbfbca4701b7ff99dbed9d00b6
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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