Water → benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclopentylpropylmethylcarbamate

HRID 1254346Notes

Reaction equation

HRID 1254346 reaction equation
[CH:1]1([CH2:6][C@H:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][NH:9][CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[C:26](Cl)([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].O>C(Cl)Cl>[C:14]([O:13][C:12]([NH:11][C@@H:7]([CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH2:8][N:9]([CH3:10])[C:26](=[O:27])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:18])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 59383030tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamate

Product 1

HCID 59383026benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclopentylpropylmethylcarbamateYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamate (900 mg, 3.52 mmol) and Et3N (1.5 mL, 10.6 mmol) in CH2Cl2 (10 mL) was added dropwise a solution of CbzCl (720 mg, 4.22 mmol) in CH2Cl2 (5 mL) at 0° C. After stirring for an additional 2 h, water (30 mL) was added and the mixture was extracted with CH2Cl2 (2×10 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica chromatography to obtain benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclopentylpropylmethylcarbamate (550 mg, 40%) as an oil. 1H NMR (CDCl3, 400 MHZ) δ 1.10 (m, 2 H), 1.43 (s, 9 H), 1.49 (m, 3 H), 1.60 (m, 3 H), 1.81 (m, 3 H), 2.96 (s, 3 H), 3.15 (m, 1 H), 3.40 (m, 1 H), 3.83 (brs, 1H), 4.57 (brs, 1 H), 5.16 (s, 2 H), 7.33 (m, 5H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (2×10 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-7a4c9211d61b4e57a097034ee9db02f8
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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