Acetate → HCID 178476395, compound

HRID 1763729Notes

Reaction equation

HRID 1763729 reaction equation
Cl.[CH2:2]([NH:4][C:5](=[O:92])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:91])[C@H:12]([CH2:84][CH2:85][CH2:86][NH:87][C:88](=[NH:90])[NH2:89])[NH:13][C:14](=[O:83])[C@H:15]([CH2:79][CH:80]([CH3:82])[CH3:81])[NH:16][C:17](=[O:78])[C@@H:18]([CH2:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)[NH:19][C:20](=[O:70])[C@H:21]([CH2:62][C:63]1[CH:68]=[CH:67][C:66]([OH:69])=[CH:65][CH:64]=1)[NH:22][C:23](=[O:61])[C@H:24]([CH2:59][OH:60])[NH:25][C:26](=[O:58])[C@H:27]([CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)[NH:28][C:29](=[O:47])[C@H:30]([CH2:42][CH2:43][C:44](=[O:46])[NH2:45])[NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:3].[C:93]([O-:96])(=[O:95])[CH3:94]>CO>[C:93]([OH:96])(=[O:95])[CH3:94].[CH2:2]([NH:4][C:5](=[O:92])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:91])[C@H:12]([CH2:84][CH2:85][CH2:86][NH:87][C:88](=[NH:89])[NH2:90])[NH:13][C:14](=[O:83])[C@H:15]([CH2:79][CH:80]([CH3:81])[CH3:82])[NH:16][C:17](=[O:78])[C@@H:18]([CH2:71][C:72]1[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=1)[NH:19][C:20](=[O:70])[C@H:21]([CH2:62][C:63]1[CH:64]=[CH:65][C:66]([OH:69])=[CH:67][CH:68]=1)[NH:22][C:23](=[O:61])[C@H:24]([CH2:59][OH:60])[NH:25][C:26](=[O:58])[C@H:27]([CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)[NH:28][C:29](=[O:47])[C@H:30]([CH2:42][CH2:43][C:44](=[O:46])[NH2:45])[NH:31][C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[CH3:3]

Participants

4

Reactant 2

HCID 175AcetateHCID 178465151HCID 178465151, compound

Product 1

HCID 178476395HCID 178476395, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 300 mg. of Nα -benzyloxycarbonyl-L-glutaminyl-L-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucyl-L-arginyl-L-proline N-ethylamide hydrochloride in 100 ml. of methanol is put on a column of Dowex 1 × 2 (acetate form) resin 1.8 by 23 cm. and the material is eluted with methanol, collecting 40 ml. fractions. Fractions 2 to 5 on standing give an insoluble product. They are combined and filtered and the filtrate is concentrated to 30 ml. and diluted with ether (150 ml.). The product which precipitates is filtered off, washed with ether and dried at 50° C. under reduced pressure to give Nα -benzyloxycarbonyl-L-glutaminyl-L-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucyl-L-arginyl-L-proline N-ethylamide acetate salt [α]D23 -29° (c 1.00, DMF); λmax 289.5 E11 41.7 λmax 280 E11 54.3.

Workup

  1. washand the material is eluted with methanol
  2. customcollecting 40 ml
  3. customFractions 2 to 5 on standing give an insoluble product
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to 30 ml
  6. additionand diluted with ether (150 ml.)
  7. customThe product which precipitates
  8. filtrationis filtered off
  9. washwashed with ether
  10. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-bbe37ad126764981aeb6041fec9cf0f4
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

Loading…