Triethylamine → HCID 58649722, compound

HRID 1829911Notes

Reaction equation

HRID 1829911 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]3=[C:24]([CH3:30])[C:25](C(O)=O)=[CH:26][N:22]3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])=CC=1.CC[N:50]([CH2:53]C)CC.[C:55]([O:59][C:60]([N:62]1[CH2:67][CH2:66][O:65][CH2:64][C@@H:63]1[CH2:68][OH:69])=[O:61])([CH3:58])([CH3:57])[CH3:56]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:55]([O:59][C:60]([N:62]1[CH2:67][CH2:66][O:65][CH2:64][C@@H:63]1[CH2:68][O:69][C:53](=[O:38])[NH:50][C:25]1[C:24]([CH3:30])=[C:23]2[N:22]([CH:26]=1)[N:21]=[CH:20][N:19]=[C:18]2[NH:17][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:2]([Cl:1])[CH:3]=1)=[O:61])([CH3:58])([CH3:57])[CH3:56]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide2×HCID 1514266tert-Butyl (3S)-3-(hydroxymethyl)morpholine-4-carboxylateHCID 22055270HCID 22055270, compound

Product 1

HCID 58649722HCID 58649722, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4C (150 mg, 0.35 mmol), DPPA (0.11 ml, 0.53 mmol) and Et3N (0.12 ml, 0.88 mmol) in toluene (3.5 ml) was heated at 55° C. for 3 h. Additional DPPA (0.02 ml, 0.10 mmol) was added, and the mixture was stirred at this temperature for another 1 h. (S)-3-Hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (115 mg, 0.53 mmol) was added, and the resulting mixture was heated at 80° C. overnight. The mixture was cooled to rt, diluted with EtOAc (80 ml), washed with H2O (1×30 ml), saturated Na2CO3 (2×30 ml) and brine (1×30 ml). The mixture was dried (MgSO4), filtered and concentrated. The residue was triturated in MTBE (20 ml) and filtered to give 4D (124 mg, 55%) which was used in the next step without further purification.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated at 80° C. overnight
  3. temperatureThe mixture was cooled to rt
  4. washwashed with H2O (1×30 ml), saturated Na2CO3 (2×30 ml) and brine (1×30 ml)
  5. dry with materialThe mixture was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated in MTBE (20 ml)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2f52fb09b2a04b579266b6dd682cc572
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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