Morpholine → HCID 178472441, compound

HRID 1613488Notes

Reaction equation

HRID 1613488 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH:7]([CH2:28][C:29]([OH:31])=O)[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.C(OCC)C>[C:1]([O:5][C:6](=[O:32])[CH:7]([CH2:28][C:29]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:31])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:17][CH2:18][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178472443HCID 178472443, compound

Product 1

HCID 178472441HCID 178472441, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Carboxymethyl)-3-{1-[(cis-4-ethoxycarbonyl-cyclohexyl)carbamoyl]cyclopentyl}propanoic acid t-butyl ester (1.0 g, 2.21 mmole) was added to a solution of morpholine (230 mg, 2.65 mmole), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride salt (845 mg, 4.41 mmole), 1-hydroxybenzotriazole hydrate (675 mg, 4.41 mmole) and triethylamine (893 mg, 8.84 mmole) in dry dichloromethane (50 ml) at room temperature. After 4 days the solvent was evaporated and the residue taken up in ethyl acetate (50 ml) and washed with 1N hydrochloric acid (50 ml), water (50 ml) and saturated sodium hydrogen carbonate solution (50 ml). The organic layer was separated, dried over magnesium sulphate and evaporated to give an orange oil. Chromatography on silica gel eluting with diethyl ether followed by ethyl acetate gave the title product as a yellow foam (790 mg, 68%). Found: C,64.63; H,9.09; N,5.23. C28H46N2O7 requires C,64.34; H,8.87; N,5.36%.

Workup

  1. customAfter 4 days the solvent was evaporated
  2. washwashed with 1N hydrochloric acid (50 ml), water (50 ml) and saturated sodium hydrogen carbonate solution (50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto give an orange oil

Sources & evidence

ORD record
ord-8c10293b284c40ee9d1b7ebea7f59aed
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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