Triethylamine → HCID 59953557, compound

HRID 325242Notes

Reaction equation

HRID 325242 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])[CH:15]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.Cl.C[O:44][C:45](=[O:52])[C@H:46]([CH2:48][CH2:49][S:50][CH3:51])[NH2:47].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CCOC(C)=O.O>[CH2:1]([N:8]1[C:12]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH:47][C@H:46]([C:45]([OH:44])=[O:52])[CH2:48][CH2:49][S:50][CH3:51])=[O:19])=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])[CH:15]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 22001320HCID 22001320, compound

Product 1

HCID 59953557HCID 59953557, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 50 mL round-bottom flasks was charged with 4-(1-benzyltetrazol-5-ylmethyl)-2-(2-methylphenyl)benzoic acid (205.1 mg, 0.52 mmol), 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (EDAC) (110.1 mg, 0.0.572 mmol), L-methionine methyl ester hydrochloride (135.0 mg, 0.676 mmol), 1-hydroxybenzotriazole (78.6 mg, 0.572 mmol) and dmf (3 mL). The reagents were stirred until completely dissolved and then triethylamine (0.14 mL, 0.936mmol) was added. The reaction was stirred about 48 h until no starting material was present. Water (2 mL) and EtOAc (2 mL) were added to dissolve the precipitate. The mixture was extracted with EtOAc (3×10 mL). The combined organic layers were washed with 2 M Na2CO3 (10 mL), water (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated under vacuum. Yield: 273.0 mg , yellow solid. 1H NMR (δ, CDCl3): 8.0 (2H), 7.0-7.4 (10H), 5.85 (1H), 5.7 (2H), 4.6 (1H), 4.3 (2H), 3.65 (3H), 1.95-2.2 (6H), 1.5-1.9 (4H).

Workup

  1. dissolutionuntil completely dissolved
  2. stirringThe reaction was stirred about 48 h until no starting material
  3. dissolutionto dissolve the precipitate
  4. extractionThe mixture was extracted with EtOAc (3×10 mL)
  5. washThe combined organic layers were washed with 2 M Na2CO3 (10 mL), water (10 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fc0ace8e83804267a13d15dcad61490e
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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