Diisopropylethylamine → 2(S)-Benzyloxycarbonylamino-3-(2-benzyloxy-5-iodophenyl)propionic acid

HRID 269600Notes

Reaction equation

HRID 269600 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[NH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:18]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]([OH:15])=[O:14].[CH2:32]([O:39][C:40](N1C(=O)CCC1=O)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:32]([O:39][C:40]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:18]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]([OH:15])=[O:14])=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 574636092(S)-Amino-3-(2-benzyloxy-5-iodophenyl)propionic acid hydrochloride

Product 1

HCID 668797412(S)-Benzyloxycarbonylamino-3-(2-benzyloxy-5-iodophenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.25 ml (53.09 mol) of N,N-diisopropylethylamine are added to a solution of 10.46 g (24.13 mmol) of 2(S)-amino-3-(2-benzyloxy-5-iodophenyl)propionic acid hydrochloride (Example 9A) in DMF. 6.615 g (26.54 mmol) of N-(benzyloxycarbonyl)succinimide (Z-OSuc) are added thereto. The resulting solution is stirred overnight and then concentrated on a rotary evaporator in vacuo. The residue is taken up in dichloromethane and extracted twice each with a 0.1N hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic phase is dried, filtered and concentrated. The mixture is purified by column chromatography on silica gel (mobile phase: cyclohexane/diethyl ether 9:1 to 8:2).

Workup

  1. concentrationconcentrated on a rotary evaporator in vacuo
  2. extractionextracted twice each with a 0.1N hydrochloric acid solution
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture is purified by column chromatography on silica gel (mobile phase: cyclohexane/diethyl ether 9:1 to 8:2)

Sources & evidence

ORD record
ord-db359ea47b9c4b929d42553bb6a1b9d1
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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