Triethylamine → HCID 69293876, compound

HRID 249626Notes

Reaction equation

HRID 249626 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:21])[CH2:6][CH2:7][O:8][CH2:9][CH:10]([NH2:20])[CH2:11][O:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:3].[C:22]([NH:32][CH2:33][CH2:34][C:35](O)=[O:36])([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(N=C=NCCCN(C)C)C.CCN(CC)CC>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH:10]([NH:20][C:35](=[O:36])[CH2:34][CH2:33][NH:32][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:9][O:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 87769910HCID 87769910, compound

Product 1

HCID 69293876HCID 69293876, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound 29 was prepared using General Procedure B with the ester hydrochloride salt (28) (1.53 g, 5.26 mmol), N-Cbz-β-alanine (1.41 g, 6.31 mmol), 1-hydrobenzotriazole (HOBt) (0.99 g, 7.36 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (1.41 g, 7.36 mmol) and Et3N (1.02 mL, 7.36 mmol) in CH2Cl2 (30 mL). Purification by flash column chromatography (on silica gel, EtOAc:n-hexane=3:1) afforded 2.39 g (92%) of the desired product (29) as a colorless liquid. 1H NMR (CDCl3): δ 7.33 (m, 5H, ArH), 6.33 (d, J=8.0 Hz, 1H, NH), 5.57 (s, 1H, NM, 5.08 (s, 2H, OCH2Ar), 4.18 (m, 1H, CH), 4.13 (q, J=7.2 Hz, 4H, CH2O), 3.70 (m, 4H, CH2O), 3.56 (m, 2H, CH2O), 3.48 (d, J=6.0, 12.0 Hz, 2H, CH2NHCO), 3.40 (m, 2H, CH2O), 2.53 (m, 4H, CH2CO), 2.42 (t, J=6.0 Hz, 2H, CH2CO), 1.25 (t, J=7.2 Hz, 6H, CH3).

Workup

  1. customThe compound 29 was prepared
  2. customPurification by flash column chromatography (on silica gel, EtOAc:n-hexane=3:1)

Sources & evidence

ORD record
ord-8186cf3f1a5044a1abc31272b3d4caff
Source dataset
uspto-grants-2011_01
Patent number
US07862807B2

Reaction notes

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