HCID 86757665, compound → HCID 59976474, compound

HRID 2269365Notes

Reaction equation

HRID 2269365 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:25][C:26](=[O:51])[C@H:27]([CH2:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C@@H:28]([N:32]([CH:40]=[O:41])[O:33]C1CCCCO1)[CH2:29][CH2:30][CH3:31])[C:17](=[O:24])[NH:18][C:19]1[S:20][CH:21]=[N:22][N:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:25][C:26](=[O:51])[C@H:27]([CH2:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C@@H:28]([N:32]([CH:40]=[O:41])[OH:33])[CH2:29][CH2:30][CH3:31])[C:17](=[O:24])[NH:18][C:19]1[S:20][CH:21]=[N:22][N:23]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86757665HCID 86757665, compound

Product 1

HCID 59976474HCID 59976474, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)hexanoic acid [(1s)-5-benzyloxycarbonylamino-1-(1,3,4-thiadiazol-2-ylcarbamoyl)-1-pentyl]amide (23 mg, 0.032 mmol) in acetic acid-water (4:1, 1 mL) is heated to 50° C. for 16 h. The reaction mixture is concentrated, then dissolved in toluene and concentrated in vacuo. The procedure is repeated once again to afford the crude product which is recrystallized from dichloromethane-methanol-diethyl ether to provide (2R,3S)-3-(formyl-hydroxyamino)-2-(3-phenyl-1-propyl)hexanoic acid [(1S)-5-benzyloxycarbonylamino-1-(1,3,4-thiadiazol-2-ylcarbamoyl)-1-pentyl]amide as a solid (14 mg, 69% yield).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutiondissolved in toluene
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product which
  5. customis recrystallized from dichloromethane-methanol-diethyl ether

Sources & evidence

ORD record
ord-9a96ede0c8754793ba530d90c9b4db52
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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