Diisopropylethylamine → HCID 178468200, compound

HRID 1375721Notes

Reaction equation

HRID 1375721 reaction equation
[Cl-].[C:2]([C@@H:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH3+:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([OH:4])=[O:3].C(N(CC)C(C)C)(C)C.[C:36]([O:40][C:41]([NH:43][C:44](=[N:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])SC)=[O:42])([CH3:39])([CH3:38])[CH3:37]>C(O)(C)C>[C:51]([O:50][C:48]([NH:47][C:44]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:22]=[CH:23][C:7]([CH2:6][C@H:5]([O:24][CH2:25][CH3:26])[C:2]([OH:4])=[O:3])=[CH:8][CH:9]=2)=[CH:20][CH:19]=1)=[N:43][C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:42])=[O:49])([CH3:54])([CH3:53])[CH3:52]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 69426610HCID 69426610, compound

Product 1

HCID 178468200HCID 178468200, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(3-{4-[(2S)-2-Carboxy-2-ethoxyethyl]phenoxy}propyl)benzenaminium chloride (152 mg, 0.4 mmol) was in isopropyl alcohol (3 ml). N,N-diisopropylethylamine (0.28 ml, 1.6 mmol) was added. The mixture was stirred for 5 minutes, then 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (290 mg, 0.4 mmol) was added. The mixture was stirred at room temperature for 7 days and thereafter evaporated in vacuum to dryness. Water and ethyl acetate were added into the residue. The mixture was acidified with 1% hydrochloric acid, pH˜5 and there was some precipitation. The two phase mixture was filtered and then separated. The pH of the water phase was further adjusted to ˜3 and the water phase was extracted with ethyl acetate (×2). All organic phases were combined and washed with brine and dried with magnesium sulfate. The solvent was evaporated in vacuum. Chromatography of the residue on an ISOLUTE column (SI, 2 g/6 ml) using heptane/DCM (50:50), then DCM and MeOH/DCM (0.5: 99.5) as eluant gave the desired product (63 mg), yield 27%.

Workup

  1. stirringThe mixture was stirred at room temperature for 7 days
  2. customevaporated in vacuum to dryness
  3. additionWater and ethyl acetate were added into the residue
  4. customsome precipitation
  5. filtrationThe two phase mixture was filtered
  6. customseparated
  7. extractionthe water phase was extracted with ethyl acetate (×2)
  8. washwashed with brine
  9. dry with materialdried with magnesium sulfate
  10. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-9d0badb5d6ec402b9bedd556b8ef91b4
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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