Triethylamine → HCID 131733610, compound

HRID 1751163Notes

Reaction equation

HRID 1751163 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17](O)=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.[NH2:47][C@H:48]([C:70]([NH2:72])=[O:71])[CH2:49][S:50][C:51]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C(Cl)Cl.C(Cl)CCl>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH:47][C@H:48]([C:70]([NH2:72])=[O:71])[CH2:49][S:50][C:51]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 13820835HCID 13820835, compoundHCID 44432703(2R)-2-amino-3-((triphenylmethyl)sulfanyl)propanamide

Product 1

HCID 131733610HCID 131733610, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Boc-Trp-Pro-OH (76 gm) and triethylamine (18.5 ml) in methylene chloride (850 ml) at about 0° C. to about −10° C., was charged EDC (54.5 gm) and HOBT (28.5 gm). Stirred for 30 minutes and charged H-Cys(Trt)-NH2 (65 gm, obtained from Ex-12) in methylene chloride (750 ml) at same temperature. After completion of the reaction organic layer was subjected to washings with aqueous sodium bicarbonate, aqueous citric acid solution. The separated organic layer was concentrated under reduced pressure and the resultant residue was crystallized in isopropyl ether to obtain Boc-Trp-Pro-Cys(Trt)-NH2 as a white solid material.

Workup

  1. washAfter completion of the reaction organic layer was subjected to washings with aqueous sodium bicarbonate, aqueous citric acid solution
  2. concentrationThe separated organic layer was concentrated under reduced pressure
  3. customthe resultant residue was crystallized in isopropyl ether

Sources & evidence

ORD record
ord-564dc02be328451ea597d0fec4143a91
Source dataset
uspto-grants-2015_10
Patent number
US09156885B2

Reaction notes

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