Acetic Acid → HCID 136207166, 화합물

HRID 2165718노트

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HRID 2165718 반응식
C([NH:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:38]=[CH:37][C:22]([C:23]([NH:25][C@H:26]([C:33]([O:35]C)=[O:34])[CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:24])=[CH:21][CH:20]=2)=[C:9]([NH:11]C(=O)C)[N:10]=1)(=O)C.C=O.[C:42]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C.CN(C)C=O>[NH2:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][N:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:25][C@H:26]([C:33]([OH:35])=[O:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:24])=[CH:37][CH:38]=2)[CH3:42])=[C:9]([NH2:11])[N:10]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 135990644HCID 135990644, 화합물

생성물 1

HCID 136207166HCID 136207166, 화합물수율 130.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 1.99 g (3.6 mmol) of dimethyl N-[4-[3-(2,4-bis(acetamido)-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoyl]-L-glutamate in 50 ml of acetonitrile and 5 ml of dimethylformamide was added 2 ml of 37% aqueous formaldehyde followed by 0.50 g (8.0 mmol) of sodium cyanoborohydride and 2 ml of acetic acid. After 18 hours the mixture was filtered to remove the solids and the filtrate was spin evaporated in vacuo. The residue was diluted with 100 ml of ice water, and then extracted with four 25 ml portions of methylene dichloride. The combined extracts were filtered through glass wool and spin evaporated in vacuo to give 2.1 g of the title compound as an oil which was a single spot on TLC. The oil was dissolved in 50 ml of ethanol and 50 ml of 1N sodium hydroxide and stirred at 70° C. for 20 hours. The reaction was cooled and spin evaporated in vacuo to a syrup. The syrup was dissolved in 50 ml of water, cooled on ice, and acidified to pH 3-4 with concentrated hydrochloric acid. The white solids were collected, washed with water, and finally with ether; yield, 1.10 g (67%), mp 190°-200° C. (one spot on TLC). Recrystallization from ethanol gave the analytical sample; yield, 0.54 g (33%, mp (166°-1678° changes to hard foam) 198°-204°; TLC (pyridine:BuOH:H2O/1:1:1); NMR (DMSO-d6) δ 8.16 (d, 1H, ArCONH), 7.71 (d, 2H, Ar), 6.66 (d, 2H, Ar), 5.94 (s, 2H, NH2), 5.76 (s, 2H, NH2) 4.36 (m, 1H, CHCO2H), 3.34 (m, 2H, CH2N(CH3)Ar), 2.93 (s, 3H, NCH3).

후처리

  1. filtrationAfter 18 hours the mixture was filtered
  2. customto remove the solids
  3. customevaporated in vacuo
  4. additionThe residue was diluted with 100 ml of ice water
  5. extractionextracted with four 25 ml portions of methylene dichloride
  6. filtrationThe combined extracts were filtered through glass wool
  7. customspin evaporated in vacuo

출처 및 근거

ORD 기록
ord-f6a39e1597484b6b85499bc8df926a8a
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940713

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