Hydrochloric Acid → HCID 23594234, compound

HRID 1612407Notes

Reaction equation

HRID 1612407 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=1)(=[O:4])=[O:3].C(OC(NCC1C=CC=CC=1CC(O)=O)=O)(C)(C)C.[ClH:36].Cl.[CH3:38][NH:39][C@@H:40]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:41][N:42]1[CH2:46][CH2:45][C@H:44]([OH:47])[CH2:43]1.CN[C@@H](C1C=CC=CC=1)CN1CCCC1.C(N(C(C)C)CC)(C)C.Cl>ClCCl.CCOCC>[ClH:36].[OH:47][C@H:44]1[CH2:45][CH2:46][N:42]([CH2:41][C@@H:40]([N:39]([CH3:38])[C:14](=[O:16])[CH2:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:12][CH:11]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:43]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 2755928(2-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)acetic acidHCID 11106482116508-51-1HCID 14180954HCID 14180954, compoundHCID 23594216HCID 23594216, compound

Product 1

HCID 23594234HCID 23594234, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 13a was prepared by following the procedure of Example 1, Step f, except 12a was substituted for 6a, 1-[2-methylamino-2-(S)-phenyl-ethyl]-pyrrolidin-3-(S)-ol dihydrochloride was substituted for methyl-[1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl]-amine and diisopropylethylamine (3.3 eq) was substituted for diisopropylethylamine (2.2 eq). The resulting oil was dissolved in dichloromethane (0.1 M) and a solution of hydrochloric acid (5.5 eq) in ether (2.0 M) was added slowly at 0° C. The solvent was removed under reduced pressure. The resulting solid was triturated with ether then filtered off to afford the product as the hydrochloric acid salt. (55%) 1H NMR (400 MHz, DMSO-d6) δ 10.22-10.72 (m, 1H), 7.55 (m, 1H), 7.18-7.42 (m, 9H), 6.17 (m, 1H), 5.42-5.62 (m, 1H), 4.44 (m, 1H), 4.13 (m, 3H), 3.84 (m, 2H), 3.40-3.72 (m, 3H), 3.17 (m, 1H), 2.83 (s, 3H), 2.76 (m, 3H), 2.09-2.35 (m, 1H), 1.89 (m, 1H). Mass Spectral Analysis m/z=446.4 (M+H)+ tR=3.45 min (98%)

Workup

  1. customCompound 13a was prepared
  2. customThe solvent was removed under reduced pressure
  3. customThe resulting solid was triturated with ether
  4. filtrationthen filtered off

Sources & evidence

ORD record
ord-97d2d04ae4bb413da3ecb5b29d9c14a9
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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