Triethylamine → HCID 178501487, compound

HRID 1606821Notes

Reaction equation

HRID 1606821 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:17]([NH:19][C@H:20]([C:31](O)=[O:32])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:18])[CH2:11][C:12]1[N:16]=[CH:15][NH:14][CH:13]=1)=[O:8].[CH3:34][O:35][C:36](=[O:41])[C@H:37]([CH2:39][OH:40])[NH2:38].C(N(CC)CC)C>C(#N)C>[CH3:34][O:35][C:36](=[O:41])[C@H:37]([CH2:39][OH:40])[NH:38][C:31](=[O:32])[C@H:20]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[NH:19][C:17](=[O:18])[C@H:10]([CH2:11][C:12]1[N:16]=[CH:15][NH:14][CH:13]=1)[NH:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH2:4][C:5](=[O:6])[NH:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoateHCID 178516178HCID 178516178, compound

Product 1

HCID 178501487HCID 178501487, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

L-Pyroglutamyl-L-histidyl-L-tryptophan (IV) (0.452 g) and L-serine methyl ester (V) hydrochloride (0.155 g) in dry acetonitrile (50 ml) are treated with triethylamine (0.14 ml) and DCI (0.227 g) in dry acetonitrile (5 ml) at 0°C. After stirring at room temperature for 24 hours, the reaction mixture is evaporated to dryness. The residue is dissolved in methanol and the dicyclohexylurea is removed by filtration. The filtrate is concentrated to dryness to L-pyroglutamyl-L-histidyl-L-tryptophyl-L-serine methyl ester (VI).

Workup

  1. customthe reaction mixture is evaporated to dryness
  2. dissolutionThe residue is dissolved in methanol
  3. customthe dicyclohexylurea is removed by filtration
  4. concentrationThe filtrate is concentrated to dryness to L-pyroglutamyl-L-histidyl-L-tryptophyl-L-serine methyl ester (VI)

Sources & evidence

ORD record
ord-dcc0778692ec436a85bd26955e83d828
Source dataset
uspto-grants-1976_04
Patent number
US03953416

Reaction notes

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