Water → HCID 20640734, compound

HRID 1263419Notes

Reaction equation

HRID 1263419 reaction equation
[NH2:1][C@H:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1.C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].O>C1COCC1>[CH2:21]([O:20][C:18]([NH:1][C@H:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 18603542(S)-4-Aminoazepan-2-one

Product 1

HCID 20640734HCID 20640734, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

(3S)-3-Amino-ε-caprolactam (25 g) and triethylamine (19.7 g) were dissolved in THF (200 ml) and cooled to 5° C. Benzyl chloroformate (33 g) in THF (50ml) was added dropwise over 30 minutes. The reaction mixture was stirred at ambient temperature for 18 hours and then poured into water (500 ml). The reaction mixture was extracted with ethyl acetate (3×100 ml). The combined extracts were dried (MgSO4) and evaporated. The residue was triturated with ether (40 ml) and filtered to give 20 g of (S)-3-benzyloxycarbonylamino-ε-caprolactam as a white solid; NMR (d6-DMSO): 1.1-2(m, 6H), 2.9-3.2(m, 2H), 4.1-4.25 (m, 1H), 5.0 (s, 2H), 7.25-7.4 (m, 5H), 7.75 (t, 1H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customThe residue was triturated with ether (40 ml)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7655b6b5fbc54604aafa61b3889a2119
Source dataset
uspto-grants-2003_04
Patent number
US06541453B2

Reaction notes

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