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Triethylamine → HCID 13934655, compound

HRID 652083
Notes
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Reaction equation

HRID 652083 reaction equation
P(Cl)(=O)[O-].[C:5]1([CH2:11][O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]([OH:38])[C:21]([N:23]2[CH2:37][CH2:36][CH2:35][C@H:24]2[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:22])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:55]([O:63][CH:64]([P:69](OC)([O:71][CH:72](NC(OCC1C=CC=CC=1)=O)CCCCC([C@]1(C(OCC2C=CC=CC=2)=O)CCCN1)=O)=[O:70])[CH2:65][CH2:66][CH2:67][CH3:68])(=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>C(Cl)Cl>[C:55]([O:63][CH:64]([P:69]([O:71][CH3:72])([O:38][C@@H:20]([CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:13]([O:12][CH2:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:14])[C:21]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:22])=[O:70])[CH2:65][CH2:66][CH2:67][CH3:68])(=[O:62])[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 13934652HCID 13934652, compoundHCID 131715172HCID 131715172, compoundHCID 178527057HCID 178527057, compound

Product 1

HCID 13934655HCID 13934655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The resulting crude phosphonochloridate is taken up in dry methylene chloride (2 ml.) and added dropwise to a methylene chloride (8 ml.) solution of 1-[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-hydroxy-1-oxohexyl]-L-proline, phenylmethyl ester (1.97 g., 4.2 mmole), triethylamine (0.66 g., 6.5 mmole) and dimethylaminopyridine (0.1 g.) at 0° under argon and stirred at 0°-15° for 2 hours. The mixture is partitioned between methylene chloride and 5% potassium bisulfate. The organic phase is washed with brine, dried over magnesium sulfate, and evaporated to dryness. The resulting crude oil is purified by chromatography (LPS-1 silica gel) eluting with (7:3) hexane:acetone. The product containing fractions are combined and concentrated in vacuo to yield 1.55 g. of 1-[(S)-2-[[[1-(benzoyloxy)pentyl]methoxyphosphinyl]oxy-1-oxo-6-[[(phenylmethoxy)carbonyl]amino]hexyl]-L-proline, phenylmethyl ester.

Workup

  1. customThe mixture is partitioned between methylene chloride and 5% potassium bisulfate
  2. washThe organic phase is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe resulting crude oil is purified by chromatography (LPS-1 silica gel)
  6. washeluting with (7:3) hexane
  7. additionThe product containing fractions
  8. concentrationconcentrated in vacuo
  9. customto yield 1.55 g

Sources & evidence

ORD record
ord-e103290f9c364a438419eee0bb8b7838
Source dataset
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04670422

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes