Pyrrole-2-Carboxylic Acid → HCID 69818121, compound

HRID 2417447Notes

Reaction equation

HRID 2417447 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([N:12]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:13][C@H:14]([OH:31])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1.[NH:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[C:44](O)=[O:45].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(=O)([O-])O.[Na+]>[CH2:32]([N:12]([C@H:9]([CH2:10][OH:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:44]([C:40]2[NH:39][CH:43]=[CH:42][CH:41]=2)=[O:45])=[CH:3][CH:4]=1)[CH2:13][C@H:14]([OH:31])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][CH:18]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 12473Pyrrole-2-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69817892HCID 69817892, compound

Product 1

HCID 69818121HCID 69818121, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred suspension of (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino]-1-propanol (51.3 mg), 1H-pyrrole-2-carboxylic acid (11.9 mg) and 1-hydroxybenzotriazole hydrate (13.5 mg) in 1,2-dichloromethane (1.0 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (21.5 mg) under ice-cooling and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The extracts were combined, washed twice with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (eluent: toluen/ethyl acetate=5/5) to give N-[4-[(2S)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]-amino]-3-hydroxypropyl]phenyl]-1H-pyrrole-2-carboxamide (43 mg) as a gum.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. washwashed twice with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (eluent: toluen/ethyl acetate=5/5)

Sources & evidence

ORD record
ord-9e9495a29f184dc69721646dce7db1d1
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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