Triethylamine → HCID 21074411, compound

HRID 1768870Notes

Reaction equation

HRID 1768870 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:23][C@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1.ClC(OCC(C)C)=O.C(N(CC)CC)C>O1CCCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][C@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 21074411HCID 21074411, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Condensation of Z-Phe-OH (15.0 g.) and H-Trp-OCH3 (12.8 g.) by the mixed anhydride method using isobutyl chloroformate (6.52 ml.) and triethylamine (10.1 g.) in tetrahydrofuran for a few minutes at -20° C. and then for about 1 hr. at room temperature, isolation of the crude product by ethyl acetate extraction, and purification by crystallization from ether-hexane gave Z-Phe-Trp-OCH3 (21.5 g., 8670 yield).

Workup

  1. customfor a few minutes
  2. customat -20° C.
  3. extractionat room temperature, isolation of the crude product by ethyl acetate extraction, and purification
  4. customby crystallization from ether-hexane

Sources & evidence

ORD record
ord-7de5f6377aa540b5adefe7be99260109
Source dataset
uspto-grants-1995_01
Patent number
US05378803

Reaction notes

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