Triethylamine → HCID 86745456, compound

HRID 1534149Notes

Reaction equation

HRID 1534149 reaction equation
C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[NH2:27][C@@H:28]1[CH2:32][C@H:31]([CH2:33][OH:34])[CH:30]=[CH:29]1.[Cl:35][C:36]1[C:41]([NH:42][CH:43]=[O:44])=[C:40](Cl)[N:39]=[C:38]([NH:46][C:47](=[O:49])[CH3:48])[N:37]=1.C(N(CC)CC)C>O.C(O)C>[Cl:35][C:36]1[C:41]([NH:42][CH:43]=[O:44])=[C:40]([NH:27][C@H:28]2[CH2:32][C@@H:31]([CH2:33][OH:34])[CH:30]=[CH:29]2)[N:39]=[C:38]([NH:46][C:47](=[O:49])[CH3:48])[N:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 16638380HCID 16638380, compoundHCID 130298492HCID 130298492, compound

Product 1

HCID 86745456HCID 86745456, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(1S,4R)-4-Amino-2-cyclopentene-1-methanol dibenzoyl-D-tartrate prepared as described in Example 13 (2.76 g, 9.02 mmol) was dissolved in water (20 ml) and applied to a column of 65 ml of Amberlite IA-400 (OH- form) anion exchange resin. The column was washed with water. Basic fractions were combined and evaporated to a residual oil which was dried by evaporation of absolute ethanol and then at 0.5 mm to give oil (darkens rapidly in air) which was used immediately. This oil was dissolved in ethanol (5 ml) and added to a solution of N-(4,6-dichloro-5-formamido-2-pyrimidinyl)acetamide (2.07 g, 8.31 mmol), prepared as described in Example 15, and triethylamine (2.50 g, 24.8 mmol). The resulting dark solution was heated (oil bath 75°-80° C.) under nitrogen for 50 minutes. The solution was evaporated to a syrup which was applied to a silica gel column. Title compound was eluted with 3 to 5% methanol-chloroform as a pale yellow solid foam (1.59 g, 54%); 1H-NMR identical with that of crystallized sample. Such a sample was crystallized from ethanol to give white granules, m.p. 194°-195° C.; 1H-NMR (DMSO-d6) identical with that of the title compound of Example 15; [α]20D +2.7°, [α]54620 +2.9°, [α]43620 -2.5°, [α]36520 -41.2° (c=0.238, methanol).

Workup

  1. washThe column was washed with water
  2. customevaporated to a residual oil which
  3. dry with materialwas dried by evaporation of absolute ethanol
  4. customat 0.5 mm to give oil (darkens rapidly in air) which
  5. customprepared
  6. temperatureThe resulting dark solution was heated (oil bath 75°-80° C.) under nitrogen for 50 minutes
  7. customThe solution was evaporated to a syrup which
  8. washTitle compound was eluted with 3 to 5% methanol-chloroform as a pale yellow solid foam (1.59 g, 54%)
  9. customSuch a sample was crystallized from ethanol
  10. customto give white granules, m.p. 194°-195° C.

Sources & evidence

ORD record
ord-13a1a5a0d2044ce1982b66393bf6799b
Source dataset
uspto-grants-1992_02
Patent number
US05087697

Reaction notes

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