Triethylamine → HCID 53706586, compound

HRID 1283850Notes

Reaction equation

HRID 1283850 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH:20]([C:21]([O:23]C(C)(C)C)=[O:22])[CH2:19][CH2:18][NH:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:36]([O:43][C:44](Cl)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[C:1]1([CH2:7][O:8][C:9](=[O:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH:20]([C:21]([OH:23])=[O:22])[CH2:19][CH2:18][N:17]2[C:44]([O:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:45])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 54268713HCID 54268713, compound

Product 1

HCID 53706586HCID 53706586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 17 (0.1 mol.) is added to a mixture of dichloromethane (200 ml.), triethylamine (0.11 mol.) and benzyloxycarbonyl chloride. The mixture is stirred for 2 hours at room temperature, washed with 5% potassium bisulfate, water, dried, and concentrated to dryness. The residue, 3-(t-butoxycarbonyl)-1-[(phenylmethyloxy)carbonyl]-2-pyrrolidineheptanoic acid phenylmethyl ester is dissolved in trifluoroacetic acid and the solution stored at room temperature for 1 hour. The solution is concentrated to dryness in vacuo yielding 3-carboxy-1-[(phenylmethyloxy)carbonyl]-2-pyrrolidineheptanoic acid phenylmethyl ester.

Workup

  1. washwashed with 5% potassium bisulfate, water
  2. customdried
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue, 3-(t-butoxycarbonyl)-1-[(phenylmethyloxy)carbonyl]-2-pyrrolidineheptanoic acid phenylmethyl ester is dissolved in trifluoroacetic acid
  5. waitthe solution stored at room temperature for 1 hour
  6. concentrationThe solution is concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b7058ab23a1a415a98577aa8c9b6ae23
Source dataset
uspto-grants-1976_08
Patent number
US03976660

Reaction notes

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