Ethylenediaminetetraacetic Acid → N-Acetyltryptamine

HRID 1603751

Reaction equation

HRID 1603751 reaction equation
C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)O[CH2:21][C@H:22]1O[C@@H:25]([N:27]2[C:36]3N=CN=[C:31](N)[C:30]=3N=C2)[C@H:24](O)[C@@H:23]1OP(O)(O)=O)(=O)C.Cl.NCC[C:56]1[C:64]2[C:59](=CC=CC=2)[NH:58][CH:57]=1.CCNC(CCNC([C@H](O)C(COP(OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)(O)=O)(O)=O)(C)C)=O)=[O:69].C1C(SSC2C=CC([N+]([O-])=O)=C(C(O)=O)C=2)=CC(C(O)=O)=C([N+]([O-])=O)C=1.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].SC[C@H]([C@@H](CS)O)O.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C1C=CC2NC=C(CCO)C=2C=1.C[14C](SCCNC(CCNC([C@H](O)C(COP(OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)(O)=O)(O)=O)(C)C)=O)=O)=O.C(OC(=O)C)(=O)C>C(N(CC)CC)C>[C:59]([NH:58][CH2:57][CH2:56][C:24]1[C:23]2[C:36](=[CH:30][CH:31]=[CH:21][CH:22]=2)[NH:27][CH:25]=1)(=[O:69])[CH3:64]

Participants

12

Reactant 10

HCID 6049Ethylenediaminetetraacetic AcidHCID 62545,5'-Dithiobis(2-nitrobenzoic Acid)HCID 7918Acetic AnhydrideHCID 10685TryptopholHCID 24243Trisodium PhosphateHCID 67652Tryptamine hydrochloride2×HCID 165363Adenosine 5'-(trihydrogen diphosphate), 3'-(dihydrogen phosphate), P'-((3R)-4-((3-(ethylamino)-3-oxopropyl)amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl) esterHCID 444493acetyl CoAHCID 446094D-1,4-DithiothreitolHCID 73755097HCID 73755097, compound

Product 1

HCID 70547N-AcetyltryptamineYield 88%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The following were purchased: acetyl-CoA (Pharmacia Biotech Inc.); tryptamine-HCl, desulfo-CoA, glutathione-agarose, DTNB (Sigma); sodium phosphate, dithiothreitol, guanidinium-HCl, EDTA (Fisher Scientific); tryptophol (Aldrich); and [14C]acetyl-CoA (60 Ci/mol) (NEN Life Science Products). N-acetyltryptamine was synthesized by reacting tryptamine-HCl (500 mg, 2.5 mmol) with acetic anhydride (260 mg, 2.5 mmol) in the presence of excess triethylamine (1.75 ml). After vigorous stirring at room temperature for 50 min, the mixture was partitioned between ethyl acetate (80 ml) and water (70 ml). The organic phase was washed with saturated aqueous NaHCO3 (50 ml), 0.1 M HCl (50 ml), Na2SO4 (anhydride), and the resultant was concentrated in vacuo to afford N-acetyltryptamine as off-white crystals (88% yield). Purity (>95%) was established by TLC and 1H NMR.

Workup

  1. customN-acetyltryptamine was synthesized
  2. customthe mixture was partitioned between ethyl acetate (80 ml) and water (70 ml)
  3. washThe organic phase was washed with saturated aqueous NaHCO3 (50 ml), 0.1 M HCl (50 ml), Na2SO4 (anhydride)
  4. concentrationthe resultant was concentrated in vacuo

Sources & evidence

ORD record
ord-00039a8ac5c842b9bf35fb31b52ea998
Source dataset
uspto-grants-1999_11
Patent number
US05990094

Linked notes

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