Dimethylformamide → HCID 131714157, compound

HRID 2164483Notes

Reaction equation

HRID 2164483 reaction equation
CN(C=O)C.[NH2:6][C@H:7]([C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:28]([NH:30][C@H:31]([C:39]([NH:41][C@H:42]([C:49]([NH:51][C@H:52]([C:59]([NH:61][C@H:62]([C:72]([O:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)=[O:73])[CH2:63][CH2:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:60])[CH2:53][O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:50])[CH2:43][O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:40])[C@@H:32]([CH3:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:29])[CH2:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[CH3:8].[NH:81]([C:116]([CH3:118])=[O:117])[C@H:82]([C:89]([NH:91][C@H:92]([C:101]([NH:103][C@H:104]([C:106](ON1C(=O)CCC1=O)=[O:107])[CH3:105])=[O:102])[CH2:93][C:94](=[O:100])[O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:90])[CH2:83][O:84][C:85]([CH3:88])([CH3:87])[CH3:86].CCN(CC)CC>O>[NH:81]([C:116]([CH3:118])=[O:117])[C@H:82]([C:89]([NH:91][C@H:92]([C:101]([NH:103][C@H:104]([C:106]([NH:6][C@H:7]([C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:28]([NH:30][C@H:31]([C:39]([NH:41][C@H:42]([C:49]([NH:51][C@H:52]([C:59]([NH:61][C@H:62]([C:72]([O:74][C:75]1[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=1)=[O:73])[CH2:63][CH2:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:60])[CH2:53][O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:50])[CH2:43][O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:40])[C@@H:32]([CH3:38])[O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:29])[CH2:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:10])[CH3:8])=[O:107])[CH3:105])=[O:102])[CH2:93][C:94](=[O:100])[O:95][C:96]([CH3:97])([CH3:98])[CH3:99])=[O:90])[CH2:83][O:84][C:85]([CH3:87])([CH3:88])[CH3:86]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13501924HCID 13501924, compoundHCID 131714155HCID 131714155, compound

Product 1

HCID 131714157HCID 131714157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The DMF-containing solution of H-Ala-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 (~16.8 mmol) from the preceeding step was cooled to 0° and Ac-Ser(tBu)-Asp(OtBu)-Ala-OSu, VII, (10.92 g, 20.16 mm, 1.2 eq.) added. Stirring proceeded at 0° for 30 min and 25° for 17 h while the pH was maintained at ~8 by addition of Et3N. Water (2.4 L) was added with stirring and the product was collected by filtration and dried in vacuo. The solid was crushed and washed with CH3OH (3×200 mL) and dried in vacuo. Yield: 23.0 g (91.7%); mp 255°-256°; Rf 0.48 (CHCl3 :CH3OH:AcOH; 80-5-1); [α]D25 -25.60° (c 1, TFE). Anal. calc. for C73H122N10O22 (1491.86): C, 58.77; H, 8.24; N, 9.39. Found: C, 58.54; H, 8.23; N, 9.43.

Workup

  1. temperaturewas cooled to 0°
  2. stirringwith stirring
  3. filtrationthe product was collected by filtration
  4. customdried in vacuo
  5. customThe solid was crushed
  6. washwashed with CH3OH (3×200 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3e96320a27d3442e939d99e5c69c2b45
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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