Ammonia → HCID 131714506, compound

HRID 1285363Notes

Reaction equation

HRID 1285363 reaction equation
[NH:1]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@H:2]([C:6]([N:8]1[CH2:57][CH2:56][CH2:55][C@H:9]1[C:10]([N:12]1[CH2:54][CH2:53][CH2:52][C@H:13]1[C:14]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:40]([NH:42][C@H:43]([C:48]([O:50]C)=O)[CH2:44][CH2:45][S:46][CH3:47])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[NH3:65]>CO.C(O)CO>[NH:1]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@H:2]([C:6]([N:8]1[CH2:57][CH2:56][CH2:55][C@H:9]1[C:10]([N:12]1[CH2:54][CH2:53][CH2:52][C@H:13]1[C:14]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:40]([NH:42][C@H:43]([C:48]([NH2:65])=[O:50])[CH2:44][CH2:45][S:46][CH3:47])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 131714504HCID 131714504, compound

Product 1

HCID 131714506HCID 131714506, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

5.00 g (4.28 mmol) of BOC-Val-Pro-Pro-Leu-Gly-Trp-Met-OMe (XI) prepared in Example 1, Step 11, were dissolved in a solution of 100 ml of methanol and 2 ml of ethylene glycol, and saturated at 0° C. with ammonia. The reaction mixture was kept in the refrigerator for 3 days, and then the excess of ammonia and the solvent were removed in vacuo. The crude product was partially purified by column chromatography on silica gel (Merck) 0.040-0.063 mm eluting with AcOEt:MeOH=87:13 and used as such in the next Step (2.58 g of compound XV were obtained from iPrOH/iPr2O): RfC 0.31.

Workup

  1. customsaturated at 0° C.
  2. customthe excess of ammonia and the solvent were removed in vacuo
  3. customThe crude product was partially purified by column chromatography on silica gel (Merck) 0.040-0.063 mm
  4. washeluting with AcOEt

Sources & evidence

ORD record
ord-73ec17d79de448aabb88b80e6a2b3227
Source dataset
uspto-grants-1986_01
Patent number
US04567162

Reaction notes

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