Triethylamine → HCID 178468983, compound

HRID 1635553Notes

Reaction equation

HRID 1635553 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][C:3]=1[N:13]1[CH:17]([OH:18])[CH2:16][CH:15](C)[C:14]1=O.[C:21]([O:25][C:26]([NH:28][C:29](=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])SC)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C.[C:47](OCC)(=[O:49])C>CN(C)C=O>[C:21]([O:25][C:26]([NH:28][C:29]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][C:3]=1[N:13]1[CH:14]([CH2:47][OH:49])[CH2:15][CH2:16][C:17]1=[O:18])=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 18676071HCID 18676071, compound

Product 1

HCID 178468983HCID 178468983, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The above amine (0.315 g, 1.13 mmol) was dissolved in dry dimethylformamide (12 mL), cooled to 0° C. with an ice bath and then treated with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (Aldrich, 0.493 g, 1.70 mmol), triethylamine (0.358 g, 3.50 mmol), and mercuric chloride (0.369 g, 1.36 mmol). The ice bath was removed and the reaction mixture was stirred under nitrogen at room temperature for 20 h. To the tan reaction mixture was added ethyl acetate (95 mL), and the mixture filtered through a bed of Celite®. The yellow filtrate was washed with water (50 mL), saturated sodium chloride (50 mL), and water (50 mL). The combined aqeuous layers were extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The crude yellow oil was purified by flash chromatography using 80% ethyl acetate/hexane to give 0.360 g (61%) of 1-{2-{[(tert-butoxycarbonylamino)(tert-butoxycarbonylimino)-methyl]amino}-4-ethoxycarbonylphenyl}-5-hydroxymethylpyrrolidin-2-one as a foamy, yellow solid, mp 104-110° C.

Workup

  1. customThe ice bath was removed
  2. customTo the tan reaction mixture
  3. filtrationthe mixture filtered through a bed of Celite®
  4. washThe yellow filtrate was washed with water (50 mL), saturated sodium chloride (50 mL), and water (50 mL)
  5. extractionThe combined aqeuous layers were extracted with ethyl acetate (2×25 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. customThe crude yellow oil was purified by flash chromatography

Sources & evidence

ORD record
ord-f858d203ae9c4776909016402d45b59e
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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