Triethylamine → HCID 178453758, compound

HRID 530145Notes

Reaction equation

HRID 530145 reaction equation
Cl.Cl.[C:3](O)(=[O:24])[C:4]1[CH:23]=[CH:22][C:7]([NH:8][CH2:9][C:10]2[N:21]=[C:20]3[C:13]([N:14]=[C:15]([NH:17][C:18]3=[O:19])[NH2:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[NH2:33][C@H:34]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:35][CH2:36][C:37](=[O:58])[NH:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54]>CN(C)C=O.C(OCC)C>[NH2:16][C:15]1[N:17]=[C:18]([OH:19])[C:20]2[C:13](=[N:12][CH:11]=[C:10]([CH2:9][NH:8][C:7]3[CH:22]=[CH:23][C:4]([C:3]([NH:33][C@H:34]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:35][CH2:36][C:37](=[O:58])[NH:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][NH:50][C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:24])=[CH:5][CH:6]=3)[N:21]=2)[N:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90418780(5)-Tert-butyl 21-amino-2,2-dimethyl-4,18-dioxo-3,8,11,14-tetraoxa-5,17-diazadocosan-22-oateHCID 136501995Pteroic acid dihydrochloride

Product 1

HCID 178453758HCID 178453758, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

To pteroic acid dihydrochloride (424 mg, 1.10 mmol) and triethylamine (0.75 mL, 5.50 mmol) in N,N-dimethylformamide (10 mL), propanephosphonic anhydride 50% solution in N,N-dimethylformamide (1.30 mL, 2.23 mmol) was added. After the reaction stirred for 45 minutes at ambient temperature, (5)-tert-butyl 21-amino-2,2-dimethyl-4,18-dioxo-3,8,11,14-tetraoxa-5,17-diazadocosan-22-oate (802 mg, 1.68 mmol) in N,N-dimethylformamide (5 mL) was added, and the reaction was stirred for 16 h at ambient temperature. After this time, the reaction was diluted with diethyl ether (150 mL) and the filtered to give (S)-tert-butyl 21-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)-2,2-dimethyl-4,18-dioxo-3,8,11,14-tetraoxa-5,17-diazadocosan-22-oate (849 mg, obtained as a 1:1 mixture with pteroic acid, 50%) as a brown solid that was used in the next step without further purification: MM-APCI MS m/z=794 [M+Na]+.

Workup

  1. stirringthe reaction was stirred for 16 h at ambient temperature
  2. filtrationthe filtered

Sources & evidence

ORD record
ord-eff7b58e0c254f00a04d35c577ab2f57
Source dataset
uspto-grants-2016_05
Patent number
US09352049B2

Reaction notes

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