Triethylamine → N-t-butoxycarbonyl-L-alanylglycine iodopropargyl ester

HRID 1656155노트

반응식

HRID 1656155 반응식
FC(F)(F)C(O)=O.[I:8][CH:9]([O:12][C:13](=[O:16])[CH2:14][NH2:15])[C:10]#[CH:11].C(N(CC)CC)C.[C:24]([O:28][C:29]([NH:31][C@H:32]([C:34](O)=[O:35])[CH3:33])=[O:30])([CH3:27])([CH3:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[I:8][CH:9]([O:12][C:13](=[O:16])[CH2:14][NH:15][C:34](=[O:35])[C@H:32]([CH3:33])[NH:31][C:29]([O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:30])[C:10]#[CH:11]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86747289Glycine iodopropargyl ester trifluoroacetate2회

생성물 1

HCID 86747290N-t-butoxycarbonyl-L-alanylglycine iodopropargyl ester수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a magnetically stirred, anhydrous dichloromethane (20 ml.) solution of glycine iodopropargyl ester trifluoroacetate (Compound #7) (2.00 g., 5.66 mmole) held at 0° C. with an ice-bath was added triethylamine (0.79 ml., 5.67 mmole), followed by N-t-butoxycarbonyl-L-alanine (1.07 g., 5.66 mmole), 1-hydroxybenzotriazole hydrate (0.77 g., 5.70 mmole) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.30 g., 6.78 mmole). The reaction mixture was held at 5° C. for 17 hours. The resultant solution was transferred to a separatory funnel and diluted to an approximate volume of 100 ml. with dichloromethane, then washed successively with water, 10% aqueous potassium hydrogen sulfate, water, saturated aqueous sodium bicarbonate, water and a final wash with saturated aqueous sodium chloride. The organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo with a rotary evaporator to give 2.09 g. (90% yield) of the desired N-t-butoxycarbonyl-L-alanylglycine iodopropargyl ester as a dry white foam. 1H-NMR (200 MHz, CDCl3) δ=1.40, d, 3H; 1.47, 1.77, two s, 9H; 4.08, d, 2H; 4.24, m, 1H; 4.90, s, 2H; 5.06, d, 1H; 6.81, s, 1H. IR (CHCl3) 1160, 1375, 1495, 1690, 1755, 2200, 2985, 3440 cm-1.

후처리

  1. additiondiluted to an approximate volume of 100 ml
  2. washwith dichloromethane, then washed successively with water, 10% aqueous potassium hydrogen sulfate, water, saturated aqueous sodium bicarbonate, water
  3. washa final wash with saturated aqueous sodium chloride
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo with a rotary evaporator
  7. customto give 2.09 g

출처 및 근거

ORD 기록
ord-0740c66dc9ab4829bc1ab9080f610e81
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05252745

반응 노트

불러오는 중…